Host material for delayed fluorescent materials, organic light-emitting device and compound

ABSTRACT

A compound represented by (Tr)n-Z is useful as a host material for delayed fluorescent materials. Tr represents a substituted or unsubstituted triphenylenyl group, and plural Tr&#39;s existing in the general formula (1) may be the same as or different from each other. Z represents a carbonyl group or a substituted or unsubstituted, n-valent aromatic hydrocarbon group. n represents an integer of 2 to 6, but when Z is a carbonyl group, n is 2.

TECHNICAL FIELD

The present invention relates to a compound useful as a host material for delayed fluorescent materials, and to an organic light-emitting device using the compound.

BACKGROUND ART

Studies are being actively performed for enhancing the light emission efficiency of organic light-emitting devices such as an organic electroluminescence devices (organic EL devices), etc. For example, regarding the light-emitting material for use in a light-emitting layer, development of delayed fluorescent materials is under way as those that can efficiently utilize the excitation energy thereof for light emission. A delayed fluorescent material is a light-emitting material that radiates fluorescence directly from the excited singlet state and radiates fluorescence (delayed fluorescence) also from the excited singlet state formed through reverse intersystem crossing from the excited triplet state, and the excited triplet state can also be made to contribute toward fluorescence emission along with the excited singlet state. As an application of the delayed fluorescent material, there are seen some publications describing an organic electroluminescence device having therein a light-emitting layer formed by a combination of a delayed fluorescent material and a host material.

For example, PTL 1 describes an example of producing an organic EL device having a light-emitting layer that contains 1,3-bis(carbazol-9-yl)benzene (mCP) and a delayed fluorescent material.

PTL 2 describes an example of producing an organic EL device having a light-emitting layer that contains 4,4′-bis(N-carbazolyl)biphenyl (CBP) and a delayed fluorescent material.

CITATION LIST Patent Literature

PTL 1: JP-A 2013-253121

PTL 2: JP-A 2013-256490

SUMMARY OF INVENTION Technical Problem

As described above, PTL 1 describes formation of a light-emitting layer by combining a delayed fluorescent material and mCP, and PTL 2 describes formation of a light-emitting layer by combining a delayed fluorescent material and CBP. Here, mCP and CBP employed in these publications have heretofore been generally used as a host material for a fluorescent material and a phosphorescent material. However, the present inventors have actually investigated the organic EL devices having the host material as combined with a delayed fluorescent material, and have found that the device lifetime is only 50 hours or so and is short, and the devices are impracticable. This is considered to be because a delayed fluorescent material differs from an ordinary fluorescent material or phosphorescent material in point of the light emission mechanism and, in addition, a delayed fluorescent material greatly differs from an ordinary light-emitting material in point of the characteristics necessary for host materials and the preferred structures of the materials. However, there exists no literature that investigates the characteristics and the structures of host materials to be combined with delayed fluorescent materials, and no one could expect what type of compound would be useful as a host material for delayed fluorescent materials, and the situation is such that no one could sufficiently utilize the characteristics of delayed fluorescent materials.

Given the situation, the present inventors have made assiduous studies of investigating the usefulness of various materials as a host material for delayed fluorescent materials. With that, the inventors have hit on a general formula of a compound useful as a host material for delayed fluorescent materials, and have further promoted assiduous investigations for generalizing the constitution of an organic light-emitting device having a high light emission efficiency and a long device lifetime.

Solution to Problem

As a result of assiduous studies, the present inventors have found that, by using a compound having a structure where plural triphenylenyl groups bond via a carbonyl group or an aromatic hydrocarbon group as a host material for delayed fluorescent materials, not only the device lifetime can be more greatly prolonged than in the case of using a carbazole-type host material but also high efficiency and low-voltage driving can be expected. Based on these findings, the present inventors have now reached providing the present invention as described below as a means for solving the above-mentioned problems.

[1] A host material for delayed fluorescent materials, containing a compound represented by the following general formula (1): (Tr)_(n)-Z  General Formula (1) [In the general formula (1), Tr represents a substituted or unsubstituted triphenylenyl group, and plural Tr's existing in the general formula (1) may be the same as or different from each other. Z represents a carbonyl group or a substituted or unsubstituted, n-valent aromatic hydrocarbon group. n represents an integer of 2 to 6, but when Z is a carbonyl group, n is 2.] [2] The host material for delayed fluorescent materials according to [1], wherein Z is a substituted or unsubstituted, n-valent aromatic hydrocarbon group. [3] The host material for delayed fluorescent materials according to [2], wherein Z is an n-valent benzene residue. [4] The host material for delayed fluorescent materials according to [3], wherein Tr bonds to at least the 1-position and the 3-position of the benzene residue. [5] The host material for delayed fluorescent materials according to [2], wherein Z is an n-valent biphenyl residue. [6] The host material for delayed fluorescent materials according to [2], wherein Z is an n-valent aromatic hydrocarbon group substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. [7] The host material for delayed fluorescent materials according to [1], wherein Z is a carbonyl group. [8] The host material for delayed fluorescent materials according to [7], wherein at least one Tr has a substituent represented by the following general formula (2): Tr⁴-CO—  General Formula (2) [In the general formula (2), Tr⁴ represents a substituted or unsubstituted triphenylenyl group.] [9] The host material for delayed fluorescent materials according to [8], wherein two Tr's have, in total, 1 to 5 substituents each represented by the general formula (2). [10] The host material for delayed fluorescent materials according to any one of [7] to [9], which contains a partial structure with a carbonyl group bonding to the 2-position, the 3-position, the 6-position, the 7-position, the 10-position or the 11-position of the triphenylene ring inside the molecule. [11] The host material for delayed fluorescent materials according to [10], wherein all the carbonyl groups bonding to the triphenylene ring existing inside the molecule bond to the 2-position, the 3-position, the 6-position, the 7-position, the 10-position or the 11-position of the triphenylene ring. [12] The host material for delayed fluorescent materials according to any one of [1] to [11], wherein at least one Tr in the general formula (1) is a triphenylenyl group substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. [13] An organic light-emitting device comprising a layer that contains the host material of any one of [1] to [12] and a delayed fluorescent material. [14] The organic light-emitting device according to [13], comprising a layer that contains the host material of any one of [1] to [12] and any other host material other than that host material, and a delayed fluorescent material. [15] The organic light-emitting device according to [13] or [14], which is an organic electroluminescence device. [16] A compound represented by the following general formula (3): Tr¹-CO-Tr²  General Formula (3) [In the general formula (3), Tr¹ and Tr² each independently represent a substituted or unsubstituted triphenylenyl group, and Tr¹ and Tr² may be the same as or different from each other.] [17] A compound represented by the following general formula (4): (Tr³)_(n1)-Z  General Formula (4) [In the general formula (4), Tr³ represents a substituted or unsubstituted triphenylenyl group, and plural Tr³'s existing in the general formula (4) may be the same as or different from each other. Z¹ represents a substituted or unsubstituted n-valent aromatic hydrocarbon group. n1 represents an integer of 2 to 6. At least one of Tr³ and Z¹ is substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. When Tr³ is unsubstituted, Z¹ is a benzene ring residue substituted with a phenyl group or a methyl group and bonds to Tr³ at least at the 1-position and the 3-position, or is a biphenyl residue substituted with a phenyl group.]

Advantageous Effects of Invention

The compound of the present invention is useful as a host material for delayed fluorescent materials. In addition, the organic light-emitting device using the compound of the present invention as a host material for delayed fluorescent materials requires a low driving voltage and realizes a high light emission efficiency, and has a long device lifetime.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 This is a schematic cross-sectional view showing an example of a layer configuration of an organic electroluminescence device.

FIG. 2 This is a graph showing the lifetime characteristics of the organic electroluminescence device using the compound 1 of Example 1 and the organic electroluminescence device using the comparative compound A of Comparative Example 1.

FIG. 3 This is a graph showing the voltage-current density characteristics of the organic electroluminescence device using the compound 10 and CBP of Example 2, the organic electroluminescence device using CBP of Comparative Example 2, and the organic electroluminescence device using the comparative compound B and CBP of Comparative Example 3.

FIG. 4 This is a graph showing the current density-external quantum efficiency characteristics of the organic electroluminescence device using the compound 10 and CBP of Example 2, the organic electroluminescence device using CBP of Comparative Example 2, and the organic electroluminescence device using the comparative compound B and CBP of Comparative Example 3.

FIG. 5 This is a graph showing the lifetime characteristics of the organic electroluminescence device using the compound 10 and CBP of Example 2 and the organic electroluminescence device using CBP of Comparative Example 2.

DESCRIPTION OF EMBODIMENTS

The contents of the present invention are described in detail hereinunder. The constitutional elements may be described below with reference to representative embodiments and specific examples of the invention, but the invention is not limited to the embodiments and the examples. In the description, a numerical range expressed with reference to the expressions, an upper limit or less and/or a lower limit or more, means a range that includes the upper limit and/or the lower limit.

[Compound Represented by General Formula (1)]

The host material for delayed fluorescent materials of the present invention contains a compound represented by the following general formula (1): (Tr)_(n)-Z  General Formula (1)

In the general formula (1), Z represents a carbonyl group or a substituted or unsubstituted, n-valent aromatic hydrocarbon group.

The aromatic ring of the aromatic hydrocarbon group that Z represents may be a single-ring aromatic ring, or may be an aromatic ring of a ring-assembly structure where two or more aromatic rings bond via a single bond, such as a biphenyl ring, or may also be an aromatic ring of a polycyclic condensed structure where two or more aromatic rings are condensed such as naphthalene. Specifically, the aromatic hydrocarbon group is preferably an aromatic hydrocarbon group having a ring skeleton carbon number of 6 to 18. Preferably, the group is a residue of a benzene ring, a biphenyl ring, a naphthalene ring or a fluorene ring, more preferably a benzene residue or a biphenyl residue, and even more preferably a benzene residue.

When Z is a carbonyl group, n is 2.

When Z is an aromatic hydrocarbon group, n is 2 to 6, preferably 2 to 3. The bonding position of Tr in the aromatic hydrocarbon group is not specifically defined, but when Z is a benzene residue, preferably, Tr bonds to at least the 1-position and the 3-position of the residue. In the methine group and the methylene group of the aromatic hydrocarbon group to which Tr does not bond, the hydrogen atom may be substituted with a substituent, or may not be substituted. The substituent that may substitute in the aromatic hydrocarbon group includes those selected from a group of the substituents to be mentioned hereinunder, and among these, a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group is preferred. With that, the stability of the compound represented by the general formula (1) may tend to increase. The alkyl group is preferably an alkyl group having 1 to 18 carbon atoms, and is more preferably a methyl group. For the description and the preferred range of the aromatic ring that constitutes the aryl group, the description and the preferred range of the aromatic ring of the aromatic hydrocarbon group that Z may represent may be referred to. Among these, the aryl group that may substitute in the aromatic hydrocarbon group is preferably a biphenyl residue, or a benzene residue (a phenyl group), and is more preferably a phenyl group.

Tr represents a substituted or unsubstituted triphenylenyl group. The bonding position of the triphenylenyl group to Z is not specifically defined, but is preferably the 2-position. In the methine group of the triphenylenyl group that does not bond to Z, the hydrogen atom may be substituted with a substituent, or may not be substituted. The substituting position in the case where the triphenylenyl group is substituted with a substituent is preferably at least one of the 6-position, the 7-position, the 10-position and the 11-position.

The substituent that may substitute in the triphenylenyl group includes those selected from a group of the substituents to be mentioned hereinunder. Here, at least one Tr is preferably substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. With that, the stability of the compound represented by the general formula (1) may tend to increase. The alkyl group is preferably an alkyl group having 1 to 18 carbon atoms, and is more preferably a methyl group. For the description and the preferred range of the aromatic ring that constitutes the aryl group, the description and the preferred range of the aromatic ring of the aromatic hydrocarbon group that Z may represent may be referred to. Among these, the aryl group that may substitute in the triphenylenyl group is preferably a biphenyl residue, or a benzene residue (a phenyl group), and is more preferably a phenyl group.

Preferably, at least one Tr has a substituent represented by the following general formula (2). Among plural Tr's, one or more may have the substituent represented by the general formula (2), but preferably two of them have the substituent. When two Tr's have a group represented by the general formula (2), the total of the groups represented by the general formula (2) is preferably 1 to 5, more preferably 1 to 4, even more preferably 1 to 3. Tr⁴-CO—  General Formula (2)

In the general formula (2), Tr⁴ represents a substituted or unsubstituted triphenylenyl group. The bonding position to the carbonyl group (—CO—) in the triphenylenyl group is not specifically defined, but is preferably the 2-position. In the methine group not bonding to the carbonyl group in the triphenylenyl group, the hydrogen atom may be substituted with a substituent, or may not be substituted. For the description and the preferred range of the substituent that may substitute in the triphenylenyl group, the description and the preferred range of the substituent that may substitute in the triphenylenyl group of Tr may be referred to.

When plural Tr's exist inside the molecule of the compound represented by the general formula (1), the plural Tr's may be the same as or different from each other, but are preferably the same. When plural Tr⁴'s represented by the general formula (2) exist inside the molecule of the compound represented by the general formula (1), the plural Tr⁴'s may be the same as or different from each other, but are preferably the same.

The compound represented by the general formula (1) preferably contains 1 to 6 carbonyl groups, more preferably 1 to 3 carbonyl groups. Further, the compound represented by the general formula (1) preferably has a partial structure with a carbonyl group bonding to the 2-position, the 3-position, the 6-position, the 7-position, the 10-position or the 11-position of the triphenylene ring inside the molecule, and more preferably, all the carbonyl groups bonding to the triphenylene ring existing inside the molecule bond to the 2-position, the 3-position, the 6-position, the 7-position, the 10-position or the 11-position of the triphenylene ring.

Examples of the substituent of the aromatic hydrocarbon group that Z may represent, the substituent that may substitute in the triphenylenyl group of Tr and Tr⁴, and the substituent of the substituted alkyl group and the substituted aryl group that may substitute in the aromatic hydrocarbon group of the triphenylenyl group include a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, an alkyl-substituted amino group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an alkylsulfonyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an amide group, an alkylamide group having 2 to 10 carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, a trialkylsilylalkyl group having 4 to 20 carbon atoms, a trialkylsilylalkenyl group having 5 to 20 carbon atoms, trialkylsilylalkynyl group having 5 to 20 carbon atoms, a nitro group, a substituent represented by the above-mentioned general formula (2), etc. Among these examples, the substituents that may be further substituted with a substituent may be substituted. More preferred substituents include a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, and a dialkyl-substituted amino group having 1 to 20 carbon atoms. Even more preferred substituents include a fluorine atom, a chlorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, and a substituent represented by the general formula (2).

In the following, specific examples of the compound represented by the general formula (1) are exemplified. However, the compound represented by the general formula (1) that is usable in the present invention should not be interpreted in a limited way by these examples. In the compounds represented by the following formulae, R represents a methyl group, a phenyl group, a benzoyl group, a triphenylenyl group or a triphenylenylcarbonyl group. Plural R's each representing the substituent may be the same as or different from each other.

The molecular weight of the compound represented by the general formula (1) is, for example, in the case of using it by forming an organic layer that contains a compound represented by the general formula (1) according to a vapor deposition method, preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, still more preferably 800 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by the general formula (1).

The compound represented by the general formula (1) may be formed into a film according to a coating method irrespective of the molecular weight thereof. According to a coating method, even a compound having a relatively large molecular weight can be formed into a film.

By applying the present invention, it may be taken into consideration to use a compound containing plural structures represented by the general formula (1) in the molecule thereof, as a host material for delayed fluorescent materials.

For example, a polymerizable group is previously introduced in the structure represented by the general formula (1), and it may be taken into consideration to use a polymer obtained through polymerization of the polymerizable group as a host material for delayed fluorescent materials. Specifically, a monomer containing a polymerizable functional group in any of Tr and Z in the general formula (1) is prepared, and this is homo-polymerized singly or copolymerized with any other monomer to give a polymer having a repeating unit, and use of the polymer as a host material for delayed fluorescent materials may be taken into consideration. Alternatively, compounds each having a structure represented by the general formula (1) are coupled to give a dimer or a trimer, and use of these as a host material for delayed fluorescent materials may be taken into consideration.

Examples of the polymer having a repeating unit that contains a structure represented by the general formula (1) include polymers containing a structure represented by the following general formula (5) or (6).

In the general formulae (5) and (6), Q represents a group containing the structure represented by the general formula (1), and L¹ and L² each represent a linking group. The carbon number of the linking group is preferably 0 to 20, more preferably 1 to 15, even more preferably 2 to 10. The linking group preferably has a structure represented by —X¹¹-L¹¹-. Here, X¹¹ represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. L¹¹ represents a linking group, and is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group.

In the general formulae (5) and (6), R¹⁰¹, R¹⁰², R¹⁰³ and R¹⁰⁴ each independently represent a substituent. Preferably, they each are a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom or a chlorine atom, and even more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, or an unsubstituted alkoxy group having 1 to 3 carbon atoms.

The linking group represented by L¹ and L² may bond to any of Tr and Z in the structure of the general formula (1) that constitutes Q, or to Tr⁴ in the general formula (2). Two or more linking groups may bond to one Q to form a crosslinked structure or a network structure.

Specific structural examples of the repeating unit include structures represented by the following formulae (7) to (10).

Polymers having a repeating unit of the formulae (7) to (10) may be synthesized by previously introducing a hydroxy group into any of Tr and Z in a structure of the general formula (1), then introducing a polymerizable group into the structure through reaction with any of the following compounds via the hydroxy group serving as a linker, and polymerizing the polymerizable group.

The polymer having a structure represented by the general formula (1) in the molecule may be a polymer containing a repeating unit alone having a structure represented by the general formula (1) or may be a polymer containing a repeating unit having any other structure. The repeating unit having a structure represented by the general formula (1) contained in the polymer may be one type alone or may contain two or more types of repeating units. A repeating unit not having a structure represented by the general formula (1) includes those derived from monomers to be used in ordinary copolymerization. For example, there are mentioned repeating units derived from monomers having an ethylenic unsaturated bond such as ethylene, styrene, etc.

[Compound Represented by General Formula (3)]

Among the compounds represented by the general formula (1), compounds represented by the following general formula (3) are novel compounds. [Chem. 6] Tr¹-CO-Tr²  General Formula (3)

In the general formula (3), Tr¹ and Tr² each independently represent a substituted or unsubstituted triphenylenyl group, and Tr¹ and Tr² may be the same as or different from each other.

For the description and the preferred range of Tr¹ and Tr² in the general formula (3), the description of Tr in the general formula (1) may be referred to.

[Synthesis Method for Compound Represented by General Formula (3)]

The compound represented by the general formula (3) may be synthesized by combining known reactions. For example, the compound of the general formula (3) where Tr¹ and Tr² are unsubstituted triphenylenyl groups may be synthesized according to the reaction shown by the following formula.

X in the above reaction formula represents a halogen atom, including a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and is preferably a chlorine atom, a bromine atom or an iodine atom.

For the details of the reaction, Synthesis Examples to be given hereinunder may be referred to.

In addition, the compound represented by the general formula (3) may also be synthesized by combining any other known synthesis reactions.

[Compound Represented by General Formula (4)]

Among the compounds represented by the general formula (1), compounds represented by the following general formula (4) are also novel compounds. (Tr³)_(n1)-Z¹  General Formula (4)

In the general formula (4), Tr³ represents a substituted or unsubstituted triphenylenyl group, and plural Tr³'s existing in the general formula (4) may be the same as or different from each other. Z¹ represents a substituted or unsubstituted n-valent aromatic hydrocarbon group. n1 represents an integer of 2 to 6. For the description and the preferred range of Tr³, Z¹ and n1 in the general formula (4), the description of Tr, Z and n in the general formula (1) may be referred to. However, at least one of Tr³ and Z¹ is substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. Among Tr³ and Z¹, one or more Tr³'s or one Z¹ alone, or one or more Tr³'s and Z¹ may be substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. Here, when all Tr³'s are unsubstituted, Z¹ is a benzene ring residue substituted with a phenyl group or a methyl group and bonds to Tr³ at least at the 1-position and the 3-position, or is a biphenyl residue substituted with a phenyl group.

[Synthesis Method for Compound Represented by General Formula (4)]

The compound represented by the general formula (4) may be synthesized by combining known reactions. For example, a compound represented by the general formula (4) where Tr³ is an unsubstituted triphenylenyl group, Z¹ is a benzene residue with a methyl group substituting in the 5-position, and Z¹ bonds to Tr³ at the 1-position and the 3-position may be synthesized according to the reaction shown by the following formula.

X in the above reaction formula represents a halogen atom, including a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and is preferably a chlorine atom, a bromine atom or an iodine atom.

For the details of the reaction, Synthesis Examples to be given hereinunder may be referred to. In addition, the compound represented by the general formula (4) may also be synthesized by combining any other known synthesis reactions.

Triphenylene derivatives (halide derivatives, borate derivatives) that are the starting materials for synthesizing the compounds represented by the general formulae (3) and (4) can be synthesized according to the method described in PCT Int. Appl., 2013085243, PCT Int. Appl., 2013073896, PCT Int. Appl., 2012002221, or are available as commercial products.

[Organic Light-Emitting Device]

The compound represented by the general formula (1) of the invention is useful as a host material for a delayed fluorescent material in an organic light emitting device. Accordingly, the compound represented by the general formula (1) of the invention may be effectively used as host material in an organic light-emitting device that uses a delayed fluorescent material as a light-emitting material therein. For example, it is presumed that, in an organic light-emitting device having a light-emitting layer that contains a host material of the compound represented by the general formula (1) and a delayed fluorescent material, the energy generated inside the molecule of the compound represented by the general formula (1) can be efficiently transferred to the delayed fluorescent material, and accordingly, the delayed fluorescent material can efficiently radiate delayed fluorescence. Consequently, the driving voltage for the organic light-emitting device of the type is low and the device can realize a high light emission efficiency. Further, the organic light-emitting device is almost free from a problem of brightness reduction with the lapse of driving time, and can realize a long lifetime. This is presumed because the compound represented by the general formula (1) could have high stability as compared with a host material having a carbazole ring such as CBP.

Here, in order that the organic light-emitting device can express a high light emission efficiency, it is important to use a delayed fluorescent material as a light-emitting material, as combined with the compound represented by the general formula (1) of the present invention. The principle of realizing a high light emission efficiency by the use of a delayed fluorescent material may be described as follows for an organic electroluminescence device as an example.

In an organic electroluminescence device, carriers are injected from an anode and a cathode to a light emitting material to form an excited state for the light emitting material, with which light is emitted. In the case of a carrier injection type organic electroluminescence device, in general, excitons that are excited to the excited singlet state are 25% of the total excitons generated, and the remaining 75% thereof are excited to the excited triplet state. Accordingly, the use of phosphorescence, which is light emission from the excited triplet state, provides a high energy use efficiency. However, the excited triplet state has a long lifetime and thus causes saturation of the excited state and deactivation of energy through mutual action with the excitons in the excited triplet state, and therefore the quantum yield of phosphorescence may generally be often not high. A delayed fluorescent material emits fluorescent light through the mechanism that the energy of excitons transits to the excited triplet state through intersystem crossing or the like, and then transits to the excited singlet state through reverse intersystem crossing due to triplet-triplet annihilation or absorption of thermal energy, thereby emitting fluorescent light. It is considered that among the materials, a thermal activation type delayed fluorescent material emitting light through absorption of thermal energy is particularly useful for an organic electroluminescence device. In the case where a delayed fluorescent material is used in an organic electroluminescence device, the excitons in the excited singlet state normally emit fluorescent light. On the other hand, the excitons in the excited triplet state emit fluorescent light through intersystem crossing to the excited singlet state by absorbing the heat generated by the device. At this time, the light emitted through reverse intersystem crossing from the excited triplet state to the excited singlet state has the same wavelength as fluorescent light since it is light emission from the excited singlet state, but has a longer lifetime (light emission lifetime) than the normal fluorescent light and phosphorescent light, and thus the light is observed as fluorescent light that is delayed from the normal fluorescent light and phosphorescent light. The light may be defined as delayed fluorescent light. The use of the thermal activation type exciton transition mechanism may raise the proportion of the compound in the excited singlet state, which is generally formed in a proportion only of 25%, to 25% or more through the absorption of the thermal energy after the carrier injection. A compound that emits strong fluorescent light and delayed fluorescent light at a low temperature of lower than 100° C. undergoes the intersystem crossing from the excited triplet state to the excited singlet state sufficiently with the heat of the device, thereby emitting delayed fluorescent light, and thus the use of the compound may drastically enhance the light emission efficiency.

By using the compound represented by the general formula (1) of the invention as a host material for a delayed fluorescent material, there can be provided excellent organic light-emitting devices such as organic photoluminescence devices (organic PL devices), organic electroluminescence devices (organic EL devices), etc. An organic photoluminescence device has a structure that contains a substrate having formed thereon at least a light-emitting layer. An organic electroluminescence device has a structure containing at least an anode, a cathode and an organic layer formed between the anode and the cathode. The organic layer contains at least a light-emitting layer, and may be formed only of a light-emitting layer, or may have one or more organic layer in addition to the light-emitting layer. Examples of the organic layer include a hole transport layer, a hole injection layer, an electron barrier layer, a hole barrier layer, an electron injection layer, an electron transport layer and an exciton barrier layer. The hole transport layer may be a hole injection and transport layer having a hole injection function, and the electron transport layer may be an electron injection and transport layer having an electron injection function. A specific structural example of an organic electroluminescence device is shown in FIG. 1. In FIG. 1, the numeral 1 denotes a substrate, 2 denotes an anode, 3 denotes a hole injection layer, 4 denotes a hole transport layer, 5 denotes a light-emitting layer, 6 denotes an electron transport layer, and 7 denotes a cathode.

The members and the layers of the organic electroluminescence device will be described below. The descriptions for the substrate and the light-emitting layer may also be applied to the substrate and the light-emitting layer of the organic photoluminescence device.

(Substrate)

The organic electroluminescence device of the invention is preferably supported by a substrate. The substrate is not particularly limited and may be those that have been commonly used in an organic electroluminescence device, and examples thereof used include those formed of glass, transparent plastics, quartz and silicon.

(Anode)

The anode of the organic electroluminescence device used is preferably formed of as an electrode material include a metal, an alloy or an electroconductive compound each having a large work function (4 eV or more), or a mixture thereof. Specific examples of the electrode material include a metal, such as Au, and an electroconductive transparent material, such as CuI, indium tin oxide (ITO), SnO₂ and ZnO. A material that is amorphous and is capable of forming a transparent electroconductive film, such as IDIXO (In₂O₃—ZnO), may also be used. The anode may be formed in such a manner that the electrode material is formed into a thin film by such a method as vapor deposition or sputtering, and the film is patterned into a desired pattern by a photolithography method, or in the case where the pattern may not require high accuracy (for example, approximately 100 μm or more), the pattern may be formed with a mask having a desired shape on vapor deposition or sputtering of the electrode material. In alternative, in the case where a material capable of being applied as a coating, such as an organic electroconductive compound, is used, a wet film forming method, such as a printing method and a coating method, may be used. In the case where emitted light is to be taken out through the anode, the anode preferably has a transmittance of more than 10%, and the anode preferably has a sheet resistance of several hundred ohm per square or less. The thickness thereof may be generally selected from a range of from 10 to 1,000 nm, and preferably from 10 to 200 nm, while depending on the material used.

(Cathode)

The cathode is preferably formed of as an electrode material including a metal having a small work function (4 eV or less) (referred to as an electron injection metal), an alloy or an electroconductive compound, or a mixture thereof. Specific examples of the electrode material include sodium, a sodium-potassium alloy, magnesium, lithium, a magnesium-cupper mixture, a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al₂O₃) mixture, indium, a lithium-aluminum mixture, and a rare earth metal. Among these, a mixture of an electron injection metal and a second metal that is a stable metal having a larger work function than the electron injection metal, for example, a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al₂O₃) mixture, a lithium-aluminum mixture, and aluminum, are preferred from the standpoint of the electron injection property and the durability against oxidation and the like. The cathode may be produced by forming the electrode material into a thin film by such a method as vapor deposition or sputtering. The cathode preferably has a sheet resistance of several hundred ohm per square or less, and the thickness thereof may be generally selected from a range of from 10 nm to 5 μm, and preferably from 50 to 200 nm. For transmitting the emitted light, any one of the anode and the cathode of the organic electroluminescence device is preferably transparent or translucent, thereby enhancing the light emission luminance.

The cathode may be formed with the electroconductive transparent materials described for the anode, thereby forming a transparent or translucent cathode, and by applying the cathode, a device having an anode and a cathode, both of which have transmittance, may be produced.

(Light-Emitting Layer)

The light-emitting layer is a layer, in which holes and electrons injected from the anode and the cathode, respectively, are recombined to form excitons, and the layer contains a delayed fluorescent material and a host material for the delayed fluorescent material. As the host material for the delayed fluorescent material, one kind or two or more kinds selected from the group of compounds represented by the general formula (1) of the invention can be used. In order that the organic electroluminescence device and the organic photoluminescence device of the invention exhibit a high light emission efficiency, it is important that the singlet excitons and the triplet excitons generated in the delayed fluorescent material are confined in the delayed fluorescent material. Accordingly, as the host material for the delayed fluorescent material, those of the compounds represented by the general formula (1) are preferably so selected that at least any one of the excited singlet energy and the excited triplet energy thereof could be higher than that of the delayed fluorescent material. Consequently, the singlet excitons and the triplet excitons generated in the delayed fluorescent material can be confined in the molecule of the delayed fluorescent material, thereby eliciting the light emission efficiency of the material sufficiently.

In addition, the light-emitting layer may contain any other host material along with the host material for the delayed fluorescent material of the present invention. As the other host material, a compound having carrier transportability and excited energy transferability is preferably used. Accordingly, electrons and holes can be readily injected into the light-emitting layer and the probability of recombining the holes and the electrons increases. In addition, the excited energy formed by recombination of holes and electrons can be readily transferred to the delayed fluorescent material and the delayed fluorescent material can be thereby efficiently excited. As a result, the device can realize a high brightness at a low driving voltage. The host material having carrier transportability and excited energy transferability may be suitably selected from known host materials, and for the same reason as that for the compound represented by the general formula (1), it is desirable to select those of such that at least any one of the excited singlet energy and the excited triplet energy thereof is higher than that of the delayed fluorescent material. Specifically, as the other host material, a compound having a carbazole ring such as CBP or the like can be used.

In the organic light-emitting device or the organic electroluminescence device of the present invention, light emission forms from the delayed fluorescent material contained in the light-emitting layer. The light emission includes both fluorescence emission and delayed fluorescence emission. However, the light emission may partly include light emission from the compound represented by the general formula (1) as a part thereof.

The content of the delayed fluorescent material in the light-emitting layer is preferably 0.1 to 50% by mass, more preferably 0.1 to 20% by mass, even more preferably 0.5 to 5% by mass.

In the case where the host material for delayed fluorescent materials of the present invention is combined with any other host material for use herein, the ratio by mass of the two may be any arbitrary ratio, but is preferably 90/10 to 10/90, more preferably 75/25 to 25/75, even more preferably 66/33 to 33/66.

(Injection Layer)

The injection layer is a layer that is provided between the electrode and the organic layer, for decreasing the driving voltage and enhancing the light emission luminance, and includes a hole injection layer and an electron injection layer, which may be provided between the anode and the light-emitting layer or the hole transport layer and between the cathode and the light-emitting layer or the electron transport layer. The injection layer may be provided depending on necessity.

(Barrier Layer)

The barrier layer is a layer that is capable of inhibiting charges (electrons or holes) and/or excitons present in the light-emitting layer from being diffused outside the light-emitting layer. The electron barrier layer may be disposed between the light-emitting layer and the hole transport layer, and inhibits electrons from passing through the light-emitting layer toward the hole transport layer. Similarly, the hole barrier layer may be disposed between the light-emitting layer and the electron transport layer, and inhibits holes from passing through the light-emitting layer toward the electron transport layer. The barrier layer may also be used for inhibiting excitons from being diffused outside the light-emitting layer. Thus, the electron barrier layer and the hole barrier layer each may also have a function as an exciton barrier layer. The term “the electron barrier layer” or “the exciton barrier layer” referred herein is intended to include a layer that has both the functions of an electron barrier layer and an exciton barrier layer by one layer.

(Hole Barrier Layer)

The hole barrier layer has the function of an electron transport layer in a broad sense. The hole barrier layer has a function of inhibiting holes from reaching the electron transport layer while transporting electrons, and thereby enhances the recombination probability of electrons and holes in the light-emitting layer. As the material for the hole barrier layer, the materials for the electron transport layer described later may be used depending on necessity.

(Electron Barrier Layer)

The electron barrier layer has the function of transporting holes in a broad sense. The electron barrier layer has a function of inhibiting electrons from reaching the hole transport layer while transporting holes, and thereby enhances the recombination probability of electrons and holes in the light-emitting layer.

(Exciton Barrier Layer)

The exciton barrier layer is a layer for inhibiting excitons generated through recombination of holes and electrons in the light-emitting layer from being diffused to the charge transport layer, and the use of the layer inserted enables effective confinement of excitons in the light-emitting layer, and thereby enhances the light emission efficiency of the device. The exciton barrier layer may be inserted adjacent to the light-emitting layer on any of the side of the anode and the side of the cathode, and on both the sides. Specifically, in the case where the exciton barrier layer is present on the side of the anode, the layer may be inserted between the hole transport layer and the light-emitting layer and adjacent to the light-emitting layer, and in the case where the layer is inserted on the side of the cathode, the layer may be inserted between the light-emitting layer and the cathode and adjacent to the light-emitting layer. Between the anode and the exciton barrier layer that is adjacent to the light-emitting layer on the side of the anode, a hole injection layer, an electron barrier layer and the like may be provided, and between the cathode and the exciton barrier layer that is adjacent to the light-emitting layer on the side of the cathode, an electron injection layer, an electron transport layer, a hole barrier layer and the like may be provided. In the case where the barrier layer is provided, the material used for the barrier layer preferably has excited singlet energy and excited triplet energy, at least one of which is higher than the excited singlet energy and the excited triplet energy of the delayed fluorescent material, respectively.

(Hole Transport Layer)

The hole transport layer is formed of a hole transporting material having a function of transporting holes, and the hole transport layer may be provided as a single layer or plural layers.

The hole transporting material has one of injection or transporting property of holes and barrier property of electrons, and may be any of an organic material and an inorganic material. Examples of known hole transporting materials that may be used herein include a triazole derivative, an oxadiazole derivative, an imidazole derivative, a carbazole derivative, an indolocarbazole derivative, a polyarylalkane derivative, a pyrazoline derivative, a pyrazolone derivative, a phenylenediamine derivative, an arylamine derivative, an amino-substituted chalcone derivative, an oxazole derivative, a styrylanthracene derivative, a fluorenone derivative, a hydrazone derivative, a stilbene derivative, a silazane derivative, an aniline copolymer and an electroconductive polymer oligomer, particularly a thiophene oligomer. Among these, a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound are preferably used, and an aromatic tertiary amine compound is more preferably used.

Electron Transport Layer

The electron transport layer is formed of a material having a function of transporting electrons, and the electron transport layer may be provided as a single layer or plural layers.

The electron transporting material (which may also function as a hole barrier material in some cases) needs only to have a function of transporting electrons, which are injected from the cathode, to the light-emitting layer. Examples of the electron transport layer that may be used herein include a nitro-substituted fluorene derivative, a diphenylquinone derivative, a thiopyran dioxide derivative, carbodiimide, a fluorenylidene methane derivative, anthraquinodimethane and anthrone derivatives, and an oxadiazole derivative. The electron transporting material used may be a thiadiazole derivative obtained by replacing the oxygen atom of the oxadiazole ring of the oxadiazole derivative by a sulfur atom, or a quinoxaline derivative having a quinoxaline ring, which is known as an electron attracting group. Furthermore, polymer materials having these materials introduced to the polymer chain or having these materials used as the main chain of the polymer may also be used.

In the production of the organic electroluminescence device, the compound represented by the general formula (1) may be used not only in the light-emitting layer but also in the other layers than the light-emitting layer. In this case, the compound represented by the general formula (1) used in the light-emitting layer and the compound represented by the general formula (1) used in the other layers than the light-emitting layer may be the same as or different from each other. For example, the compound represented by the general formula (1) may be used in the injection layer, the barrier layer, the hole barrier layer, the electron barrier layer, the exciton barrier layer, the hole transport layer, the electron transport layer and the like described above. The film forming method of the layers are not particularly limited, and the layers may be produced by any of a dry process and a wet process.

Specific examples of preferred materials that may be used in the organic electroluminescence device are shown below, but the materials that may be used in the invention are not construed as being limited to the example compounds. The compound that is shown as a material having a particular function may also be used as a material having another function. In the structural formulae of the example compounds shown below, R, R′ and R₁ to R₁₀ each independently represent a hydrogen atom or a substituent. X represents a carbon atom or a hetero atom to form a ring skeleton, n represents an integer of 3 to 5, Y represents a substituent, and m represents an integer of 0 or more.

The delayed fluorescent material to be combined with the host material for delayed fluorescent materials that contains the compound represented by the general formula (1) is a compound capable of radiating delayed fluorescence. Preferred examples of the delayed fluorescent material are shown below, however, the delayed fluorescent material to be employed in the present invention is not limited to those shown below.

As a preferred delayed fluorescent material, a compound represented by the following general formula can be mentioned. The entire description of WO 2013/154064 including the paragraphs 0008 to 0048 and 0095 to 0133 is incorporated herein by reference as a part of the description of the present application.

[In the general formula (101), at least one of R¹ to R⁵ represents a cyano group, at least one of R¹ to R⁵ represents a group represented by the following general formula (111), and the balance of R¹ to R⁵ each represent a hydrogen atom or a substituent.]

[In the general formula (111), R²¹ to R²⁸ each independently represent a hydrogen atom or a substituent, provided that at least one of the following conditions <A> and <B> is satisfied:

<A> R²⁵ and R²⁶ together form a single bond, and

<B> R²⁷ and R²⁸ each represent an atomic group necessary for forming a substituted or unsubstituted benzene ring as combined together.]

Here, at least one of R¹ to R⁵ preferably represents a group represented by any one of the following general formulae (112) to (115).

[In the general formula (112), R³¹ to R³⁸ each independently represent a hydrogen atom or a substituent.]

[In the general formula (113), R⁴¹ to R⁴⁶ each independently represent a hydrogen atom or a substituent.]

[In the general formula (114), R⁵¹ to R⁶² each independently represent a hydrogen atom or a substituent.]

[In the general formula (115), R⁷¹ to R⁸⁰ each independently represent a hydrogen atom or a substituent.]

Specific examples of the compounds include the compounds shown in the following tables. In the case where two or more groups represented by any one of the general formulae (112) to (115) are present in the molecule of the following example compounds, all the groups have the same structure. The formulae (121) to (124) in the tables represent the following formulae, respectively, and n represents the number of the repeating units.

TABLE 1 Compound General formula (101) General formula (112) No. R¹ R² R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 1′ General General CN General General H H H H formula (112) formula (112) formula (112) formula (112) 2′ General General CN General General H CH₃ H H formula (112) formula (112) formula (112) formula (112) 3′ General General CN General General H CH₃O H H formula (112) formula (112) formula (112) formula (112) 4′ General General CN General General H H CH₃ H formula (112) formula (112) formula (112) formula (112) 5′ General General CN General General H H CH₃O H formula (112) formula (112) formula (112) formula (112) 6′ General General CN General General H H t-C₄H₉ H formula (112) formula (112) formula (112) formula (112) 7′ General General CN General General H H Cl H formula (112) formula (112) formula (112) formula (112) 8′ General General CN General General H H F H formula (112) formula (112) formula (112) formula (112) 9′ General General CN General General H H H CH₃ formula (112) formula (112) formula (112) formula (112) 10′ General General CN General General H H H CH₃O formula (112) formula (112) formula (112) formula (112) 11′ General General CN General H H H H H formula (112) formula (112) formula (112) 12′ General General CN General H H CH₃ H H formula (112) formula (112) formula (112) 13′ General General CN General H H CH₃O H H formula (112) formula (112) formula (112) 14′ General General CN General H H H CH₃ H formula (112) formula (112) formula (112) 15′ General General CN General H H H CH₃O H formula (112) formula (112) formula (112) 16′ General General CN General H H H t-C₄H₉ H formula (112) formula (112) formula (112) 17′ General General CN General H H H Cl H formula (112) formula (112) formula (112) 18′ General General CN General H H H F H formula (112) formula (112) formula (112) 19′ General General CN General H H H H CH₃ formula (112) formula (112) formula (112) 20′ General General CN General H H H H CH₃O formula (112) formula (112) formula (112) 21′ General General CN H H H H H H formula (112) formula (112) 22′ General General CN H H H CH₃ H H formula (112) formula (112) 23′ General General CN H H H CH₃O H H formula (112) formula (112) 24′ General General CN H H H H CH₃ H formula (112) formula (112) 25′ General General CN H H H H CH₃O H formula (112) formula (112) 26′ General General CN H H H H t-C₄H₉ H formula (112) formula (112) 27′ General General CN H H H H Cl H formula (112) formula (112) 28′ General General CN H H H H F H formula (112) formula (112) 29′ General General CN H H H H H CH₃ formula (112) formula (112) 30′ General General CN H H H H H CH₃O formula (112) formula (112) 31′ General H CN General H H H H H formula (112) formula (112) 32′ General H CN General H H CH₃ H H formula (112) formula (112) 33′ General H CN General H H CH₃O H H formula (112) formula (112) 34′ General H CN General H H H CH₃ H formula (112) formula (112) 35′ General H CN General H H H CH₃O H formula (112) formula (112) 36′ General H CN General H H H t-C₄H₉ H formula (112) formula (112) 37′ General H CN General H H H Cl H formula (112) formula (112) 38′ General H CN General H H H F H formula (112) formula (112) 39′ General H CN General H H H H CH₃ formula (112) formula (112) 40′ General H CN General H H H H CH₃O formula (112) formula (112) 41′ General H CN H General H H H H formula (112) formula (112) 42′ General H CN H General H CH₃ H H formula (112) formula (112) 43′ General H CN H General H CH₃O H H formula (112) formula (112) 44′ General H CN H General H H CH₃ H formula (112) formula (112) 45′ General H CN H General H H CH₃O H formula (112) formula (112) 46′ General H CN H General H H t-C₄H₉ H formula (112) formula (112) 47′ General H CN H General H H Cl H formula (112) formula (112) 48′ General H CN H General H H F H formula (112) formula (112) 49′ General H CN H General H H H CH₃ formula (112) formula (112) 50′ General H CN H General H H H CH₃O formula (112) formula (112) 51′ General H CN H H H H H H formula (112) 52′ General H CN H H H CH₃ H H formula (112) 53′ General H CN H H H CH₃O H H formula (112) 54′ General H CN H H H H CH₃ H formula (112) 55′ General H CN H H H H CH₃O H formula (112) 56′ General H CN H H H H t-C₄H₉ H formula (112) 57′ General H CN H H H H Cl H formula (112) 58′ General H CN H H H H F H formula (112) 59′ General H CN H H H H H CH₃ formula (112) 60′ General H CN H H H H H CH₃O formula (112) 61′ General General CN General F H H H H formula (112) formula (112) formula (112) 62′ General General CN General F H CH₃ H H formula (112) formula (112) formula (112) 63′ General General CN General F H CH₃O H H formula (112) formula (112) formula (112) 64′ General General CN General F H H CH₃ H formula (112) formula (112) formula (112) 65′ General General CN General F H H CH₃O H formula (112) formula (112) formula (112) 66′ General General CN General F H H t-C₄H₉ H formula (112) formula (112) formula (112) 67′ General General CN General F H H Cl H formula (112) formula (112) formula (112) 68′ General General CN General F H H F H formula (112) formula (112) formula (112) 69′ General General CN General F H H H CH₃ formula (112) formula (112) formula (112) 70′ General General CN General F H H H CH₃O formula (112) formula (112) formula (112) 71′ General General CN F F H H H H formula (112) formula (112) 72′ General General CN F F H CH₃ H H formula (112) formula (112) 73′ General General CN F F H CH₃O H H formula (112) formula (112) 74′ General General CN F F H H CH₃ H formula (112) formula (112) 75′ General General CN F F H H CH₃O H formula (112) formula (112) 76′ General General CN F F H H t-C₄H₉ H formula (112) formula (112) 77′ General General CN F F H H Cl H formula (112) formula (112) 78′ General General CN F F H H F H formula (112) formula (112) 79′ General General CN F F H H H CH₃ formula (112) formula (112) 80′ General General CN F F H H H CH₃O formula (112) formula (112) 81′ General F CN General F H H H H formula (112) formula (112) 82′ General F CN General F H CH₃ H H formula (112) formula (112) 83′ General F CN General F H CH₃O H H formula (112) formula (112) 84′ General F CN General F H H CH₃ H formula (112) formula (112) 85′ General F CN General F H H CH₃O H formula (112) formula (112) 86′ General F CN General F H H t-C₄H₉ H formula (112) formula (112) 87′ General F CN General F H H Cl H formula (112) formula (112) 88′ General F CN General F H H F H formula (112) formula (112) 89′ General F CN General F H H H CH₃ formula (112) formula (112) 90′ General F CN General F H H H CH₃O formula (112) formula (112) 91′ General F CN F General H H H H formula (112) formula (112) 92′ General F CN F General H CH₃ H H formula (112) formula (112) 93′ General F CN F General H CH₃O H H formula (112) formula (112) 94′ General F CN F General H H CH₃ H formula (112) formula (112) 95′ General F CN F General H H CH₃O H formula (112) formula (112) 96′ General F CN F General H H t-C₄H₉ H formula (112) formula (112) 97′ General F CN F General H H Cl H formula (112) formula (112) 98′ General F CN F General H H F H formula (112) formula (112) 99′ General F CN F General H H H CH₃ formula (112) formula (112) 100′ General F CN F General H H H CH₃O formula (112) formula (112) 101′ General F CN F F H H H H formula (112) 102′ General F CN F F H CH₃ H H formula (112) 103′ General F CN F F H CH₃O H H formula (112) 104′ General F CN F F H H CH₃ H formula (112) 105′ General F CN F F H H CH₃O H formula (112) 106′ General F CN F F H H t-C₄H₉ H formula (112) 107′ General F CN F F H H Cl H formula (112) 108′ General F CN F F H H F H formula (112) 109′ General F CN F F H H H CH₃ formula (112) 110′ General F CN F F H H H CH₃O formula (112) 111′ General General CN General OH H H H H formula (112) formula (112) formula (112) 112′ General General CN General OH H CH₃ H H formula (112) formula (112) formula (112) 113′ General General CN General OH H CH₃O H H formula (112) formula (112) formula (112) 114′ General General CN General OH H H CH₃ H formula (112) formula (112) formula (112) 115′ General General CN General OH H H CH₃O H formula (112) formula (112) formula (112) 116′ General General CN General OH H H t-C₄H₉ H formula (112) formula (112) formula (112) 117′ General General CN General OH H H Cl H formula (112) formula (112) formula (112) 118′ General General CN General OH H H F H formula (112) formula (112) formula (112) 119′ General General CN General OH H H H CH₃ formula (112) formula (112) formula (112) 120′ General General CN General OH H H H CH₃O formula (112) formula (112) formula (112) 121′ General General CN OH OH H H H H formula (112) formula (112) 122′ General General CN OH OH H CH₃ H H formula (112) formula (112) 123′ General General CN OH OH H CH₃O H H formula (112) formula (112) 124′ General General CN OH OH H H CH₃ H formula (112) formula (112) 125′ General General CN OH OH H H CH₃O H formula (112) formula (112) 126′ General General CN OH OH H H t-C₄H₉ H formula (112) formula (112) 127′ General General CN OH OH H H Cl H formula (112) formula (112) 128′ General General CN OH OH H H F H formula (112) formula (112) 129′ General General CN OH OH H H H CH₃ formula (112) formula (112) 130′ General General CN OH OH H H H CH₃O formula (112) formula (112) 131′ General OH CN General OH H H H H formula (112) formula (112) 132′ General OH CN General OH H CH₃ H H formula (112) formula (112) 133′ General OH CN General OH H CH₃O H H formula (112) formula (112) 134′ General OH CN General OH H H CH₃ H formula (112) formula (112) 135′ General OH CN General OH H H CH₃O H formula (112) formula (112) 136′ General OH CN General OH H H t-C₄H₉ H formula (112) formula (112) 137′ General OH CN General OH H H Cl H formula (112) formula (112) 138′ General OH CN General OH H H F H formula (112) formula (112) 139′ General OH CN General OH H H H CH₃ formula (112) formula (112) 140′ General OH CN General OH H H H CH₃O formula (112) formula (112) 141′ General OH CN OH General H H H H formula (112) formula (112) 142′ General OH CN OH General H CH₃ H H formula (112) formula (112) 143′ General OH CN OH General H CH₃O H H formula (112) formula (112) 144′ General OH CN OH General H H CH₃ H formula (112) formula (112) 145′ General OH CN OH General H H CH₃O H formula (112) formula (112) 146′ General OH CN OH General H H t-C₄H₉ H formula (112) formula (112) 147′ General OH CN OH General H H Cl H formula (112) formula (112) 148′ General OH CN OH General H H F H formula (112) formula (112) 149′ General OH CN OH General H H H CH₃ formula (112) formula (112) 150′ General OH CN OH General H H H CH₃O formula (112) formula (112) 151′ General OH CN OH OH H H H H formula (112) 152′ General OH CN OH OH H CH₃ H H formula (112) 153′ General OH CN OH OH H CH₃O H H formula (112) 154′ General OH CN OH OH H H CH₃ H formula (112) 155′ General OH CN OH OH H H CH₃O H formula (112) 156′ General OH CN OH OH H H t-C₄H₉ H formula (112) 157′ General OH CN OH OH H H Cl H formula (112) 158′ General OH CN OH OH H H F H formula (112) 159′ General OH CN OH OH H H H CH₃ formula (112) 160′ General OH CN OH OH H H H CH₃O formula (112) 161′ General General CN General Cl H H H H formula (112) formula (112) formula (112) 162′ General General CN General Cl H CH₃ H H formula (112) formula (112) formula (112) 163′ General General CN General Cl H CH₃O H H formula (112) formula (112) formula (112) 164′ General General CN General Cl H H CH₃ H formula (112) formula (112) formula (112) 165′ General General CN General Cl H H CH₃O H formula (112) formula (112) formula (112) 166′ General General CN General Cl H H t-C₄H₉ H formula (112) formula (112) formula (112) 167′ General General CN General Cl H H Cl H formula (112) formula (112) formula (112) 168′ General General CN General Cl H H F H formula (112) formula (112) formula (112) 169′ General General CN General Cl H H H CH₃ formula (112) formula (112) formula (112) 170′ General General CN General Cl H H H CH₃O formula (112) formula (112) formula (112) 171′ General General CN General F H H H H formula (112) formula (112) formula (112) 172′ General General CN General F H CH₃ H H formula (112) formula (112) formula (112) 173′ General General CN General F H CH₃O H H formula (112) formula (112) formula (112) 174′ General General CN General F H H CH₃ H formula (112) formula (112) formula (112) 175′ General General CN General F H H CH₃O H formula (112) formula (112) formula (112) 176′ General General CN General F H H t-C₄H₉ H formula (112) formula (112) formula (112) 177′ General General CN General F H H Cl H formula (112) formula (112) formula (112) 178′ General General CN General F H H F H formula (112) formula (112) formula (112) 179′ General General CN General F H H H CH₃ formula (112) formula (112) formula (112) 180′ General General CN General F H H H CH₃O formula (112) formula (112) formula (112) 181′ General General CN General CH₃O H H H H formula (112) formula (112) formula (112) 182′ General General CN General CH₃O H CH₃ H H formula (112) formula (112) formula (112) 183′ General General CN General CH₃O H CH₃O H H formula (112) formula (112) formula (112) 184′ General General CN General CH₃O H H CH₃ H formula (112) formula (112) formula (112) 185′ General General CN General CH₃O H H CH₃O H formula (112) formula (112) formula (112) 186′ General General CN General CH₃O H H t-C₄H₉ H formula (112) formula (112) formula (112) 187′ General General CN General CH₃O H H Cl H formula (112) formula (112) formula (112) 188′ General General CN General CH₃O H H F H formula (112) formula (112) formula (112) 189′ General General CN General C₂H₅O H H H CH₃ formula (112) formula (112) formula (112) 190′ General General CN General C₂H₅O H H H CH₃O formula (112) formula (112) formula (112) 191′ General General CN General C₂H₅O H H H H formula (112) formula (112) formula (112) 192′ General General CN General C₂H₅O H CH₃ H H formula (112) formula (112) formula (112) 193′ General General CN General C₂H₅O H CH₃O H H formula (112) formula (112) formula (112) 194′ General General CN General C₂H₅O H H CH₃ H formula (112) formula (112) formula (112) 195′ General General CN General C₂H₅O H H CH₃O H formula (112) formula (112) formula (112) 196′ General General CN General C₂H₅O H H t-C₄H₉ H formula (112) formula (112) formula (112) 197′ General General CN General C₂H₅O H H Cl H formula (112) formula (112) formula (112) 198′ General General CN General C₂H₅O H H F H formula (112) formula (112) formula (112) 199′ General General CN General C₂H₅O H H H CH₃ formula (112) formula (112) formula (112) 200′ General General CN General C₂H₅O H H H CH₃O formula (112) formula (112) formula (112) 201′ General General CN General C₆H₅O H H H H formula (112) formula (112) formula (112) 202′ General General CN General C₆H₅O H CH₃ H H formula (112) formula (112) formula (112) 203′ General General CN General C₆H₅O H CH₃O H H formula (112) formula (112) formula (112) 204′ General General CN General C₆H₅O H H CH₃ H formula (112) formula (112) formula (112) 205′ General General CN General C₆H₅O H H CH₃O H formula (112) formula (112) formula (112) 206′ General General CN General C₆H₅O H H t-C₄H₉ H formula (112) formula (112) formula (112) 207′ General General CN General C₆H₅O H H Cl H formula (112) formula (112) formula (112) 208′ General General CN General C₆H₅O H H F H formula (112) formula (112) formula (112) 209′ General General CN General C₆H₅O H H H CH₃ formula (112) formula (112) formula (112) 210′ General General CN General C₆H₅O H H H CH₃O formula (112) formula (112) formula (112) 211′ General General CN General Formula H H H H formula (112) formula (112) formula (112) (121) 212′ General General CN General Formula H CH₃ H H formula (112) formula (112) formula (112) (121) 213′ General General CN General Formula H CH₃O H H formula (112) formula (112) formula (112) (121) 214′ General General CN General Formula H H CH₃ H formula (112) formula (112) formula (112) (121) 215′ General General CN General Formula H H CH₃O H formula (112) formula (112) formula (112) (121) 216′ General General CN General Formula H H t-C₄H₉ H formula (112) formula (112) formula (112) (121) 217′ General General CN General Formula H H Cl H formula (112) formula (112) formula (112) (121) 218′ General General CN General Formula H H F H formula (112) formula (112) formula (112) (121) 219′ General General CN General Formula H H H CH₃ formula (112) formula (112) formula (112) (121) 220′ General General CN General Formula H H H CH₃O formula (112) formula (112) formula (112) (121) 221′ General General CN General Formula H H H H formula (112) formula (112) formula (112) (122) 222′ General General CN General Formula H CH₃ H H formula (112) formula (112) formula (112) (122) 223′ General General CN General Formula H CH₃O H H formula (112) formula (112) formula (112) (122) 224′ General General CN General Formula H H CH₃ H formula (112) formula (112) formula (112) (122) 225′ General General CN General Formula H H CH₃O H formula (112) formula (112) formula (112) (122) 226′ General General CN General Formula H H t-C₄H₉ H formula (112) formula (112) formula (112) (122) 227′ General General CN General Formula H H Cl H formula (112) formula (112) formula (112) (122) 228′ General General CN General Formula H H F H formula (112) formula (112) formula (112) (122) 229′ General General CN General Formula H H H CH₃ formula (112) formula (112) formula (112) (122) 230′ General General CN General Formula H H H CH₃O formula (112) formula (112) formula (112) (122) 231′ General General CN General Formula H H H H formula (112) formula (112) formula (112) (123) 232′ General General CN General Formula H CH₃ H H formula (112) formula (112) formula (112) (123) 233′ General General CN General Formula H CH₃O H H formula (112) formula (112) formula (112) (123) 234′ General General CN General Formula H H CH₃ H formula (112) formula (112) formula (112) (123) 235′ General General CN General Formula H H CH₃O H formula (112) formula (112) formula (112) (123) 236′ General General CN General Formula H H t-C₄H₉ H formula (112) formula (112) formula (112) (123) 237′ General General CN General Formula H H Cl H formula (112) formula (112) formula (112) (123) 238′ General General CN General Formula H H F H formula (112) formula (112) formula (112) (123) 239′ General General CN General Formula H H H CH₃ formula (112) formula (112) formula (112) (123) 240′ General General CN General Formula H H H CH₃O formula (112) formula (112) formula (112) (123) 241′ General General CN General Formula H H H H formula (112) formula (112) formula (112) (124) 242′ General General CN General Formula H CH₃ H H formula (112) formula (112) formula (112) (124) 243′ General General CN General Formula H CH₃O H H formula (112) formula (112) formula (112) (124) 244′ General General CN General Formula H H CH₃ H formula (112) formula (112) formula (112) (124) 245′ General General CN General Formula H H CH₃O H formula (112) formula (112) formula (112) (124) 246′ General General CN General Formula H H t-C₄H₉ H formula (112) formula (112) formula (112) (124) 247′ General General CN General Formula H H Cl H formula (112) formula (112) formula (112) (124) 248′ General General CN General Formula H H F H formula (112) formula (112) formula (112) (124) 249′ General General CN General Formula H H H CH₃ formula (112) formula (112) formula (112) (124) 250′ General General CN General Formula H H H CH₃O formula (112) formula (112) formula (112) (124) 251′ General General CN General General H C₆H₅ H H formula (112) formula (112) formula (112) formula (112) 252′ General General CN General General H H C₆H₅ H formula (112) formula (112) formula (112) formula (112) 253′ General General CN General H H C₆H₅ H H formula (112) formula (112) formula (112) 254′ General General CN General H H H C₆H₅ H formula (112) formula (112) formula (112) 255′ General General CN H H H C₆H₅ H H formula (112) formula (112) 256′ General General CN H H H H C₆H₅ H formula (112) formula (112) 257′ General H CN General H H C₆H₅ H H formula (112) formula (112) 258′ General H CN General H H H C₆H₅ H formula (112) formula (112) 259′ General H CN H General H C₆H₅ H H formula (112) formula (112) 260′ General H CN H General H H C₆H₅ H formula (112) formula (112) 261′ General H CN H H H C₆H₅ H H formula (112) 262′ General H CN H H H H C₆H₅ H formula (112) 263′ General General CN General F H C₆H₅ H H formula (112) formula (112) formula (112) 264′ General General CN General F H H C₆H₅ H formula (112) formula (112) formula (112) 265′ General General CN F F H C₆H₅ H H formula (112) formula (112) 266′ General General CN F F H H C₆H₅ H formula (112) formula (112) 267′ General F CN General F H C₆H₅ H H formula (112) formula (112) 268′ General F CN General F H H C₆H₅ H formula (112) formula (112) 269′ General F CN F General H C₆H₅ H H formula (112) formula (112) 270′ General F CN F General H H C₆H₅ H formula (112) formula (112) 271′ General F CN F F H C₆H₅ H H formula (112) 272′ General F CN F F H H C₆H₅ H formula (112) 273′ General General CN General OH H C₆H₅ H H formula (112) formula (112) formula (112) 274′ General General CN General OH H H C₆H₅ H formula (112) formula (112) formula (112) 275′ General General CN OH OH H C₆H₅ H H formula (112) formula (112) 276′ General General CN OH OH H H C₆H₅ H formula (112) formula (112) 277′ General OH CN General OH H C₆H₅ H H formula (112) formula (112) 278′ General OH CN General OH H H C₆H₅ H formula (112) formula (112) 279′ General OH CN OH General H C₆H₅ H H formula (112) formula (112) 280′ General OH CN OH General H H C₆H₅ H formula (112) formula (112) 281′ General OH CN OH OH H C₆H₅ H H formula (112) 282′ General OH CN OH OH H H C₆H₅ H formula (112) 283′ General General CN General Cl H C₆H₅ H H formula (112) formula (112) formula (112) 284′ General General CN General Cl H H C₆H₅ H formula (112) formula (112) formula (112) 285′ General General CN General F H C₆H₅ H H formula (112) formula (112) formula (112) 286′ General General CN General F H H C₆H₅ H formula (112) formula (112) formula (112) 287′ General General CN General CH₃O H C₆H₅ H H formula (112) formula (112) formula (112) 288′ General General CN General CH₃O H H C₆H₅ H formula (112) formula (112) formula (112) 289′ General General CN General C₂H₅O H C₆H₅ H H formula (112) formula (112) formula (112) 290′ General General CN General C₂H₅O H H C₆H₅ H formula (112) formula (112) formula (112) 291′ General General CN General C₆H₅O H C₆H₅ H H formula (112) formula (112) formula (112) 292′ General General CN General C₆H₅O H H C₆H₅ H formula (112) formula (112) formula (112) 293′ General General CN General Formula H C₆H₅ H H formula (112) formula (112) formula (112) (121) 294′ General General CN General Formula H H C₆H₅ H formula (112) formula (112) formula (112) (121) 295′ General General CN General Formula H C₆H₅ H H formula (112) formula (112) formula (112) (122) 296′ General General CN General Formula H H C₆H₅ H formula (112) formula (112) formula (112) (122) 297′ General General CN General Formula H C₆H₅ H H formula (112) formula (112) formula (112) (123) 298′ General General CN General Formula H H C₆H₅ H formula (112) formula (112) formula (112) (123) 299′ General General CN General Formula H C₆H₅ H H formula (112) formula (112) formula (112) (124) 300′ General General CN General Formula H H C₆H₅ H formula (112) formula (112) formula (112) (124)

TABLE 2 Compound General formula (101) General formula (112) No. R¹ R² R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 301 General CN General General General H H H H formula (112) formula (112) formula (112) formula (112) 302 General CN General General General H CH₃ H H formula (112) formula (112) formula (112) formula (112) 303 General CN General General General H CH₃O H H formula (112) formula (112) formula (112) formula (112) 304 General CN General General General H H CH₃ H formula (112) formula (112) formula (112) formula (112) 305 General CN General General General H H CH₃O H formula (112) formula (112) formula (112) formula (112) 306 General CN General General General H H t-C₄H₉ H formula (112) formula (112) formula (112) formula (112) 307 General CN General General General H H Cl H formula (112) formula (112) formula (112) formula (112) 308 General CN General General General H H F H formula (112) formula (112) formula (112) formula (112) 309 General CN General General General H H H CH₃ formula (112) formula (112) formula (112) formula (112) 310 General CN General General General H H H CH₃O formula (112) formula (112) formula (112) formula (112) 311 General CN General General H H H H H formula (112) formula (112) formula (112) 312 General CN General General H H H CH₃ H formula (112) formula (112) formula (112) 313 General CN General General H H H CH₃O H formula (112) formula (112) formula (112) 314 General CN General H General H H H H formula (112) formula (112) formula (112) 315 General CN General H General H H CH₃ H formula (112) formula (112) formula (112) 316 General CN General H General H H CH₃O H formula (112) formula (112) formula (112) 317 General CN H General General H H H H formula (112) formula (112) formula (112) 318 General CN H General General H H CH₃ H formula (112) formula (112) formula (112) 319 General CN H General General H H CH₃O H formula (112) formula (112) formula (112) 320 H CN General General General H H H H formula (112) formula (112) formula (112) 321 H CN General General General H H CH₃ H formula (112) formula (112) formula (112) 322 H CN General General General H H CH₃O H formula (112) formula (112) formula (112) 323 General CN General H H H H H H formula (112) formula (112) 324 General CN General H H H H CH₃ H formula (112) formula (112) 325 General CN General H H H H CH₃O H formula (112) formula (112) 326 General CN H General H H H H H formula (112) formula (112) 327 General CN H General H H H CH₃ H formula (112) formula (112) 328 General CN H General H H H CH₃O H formula (112) formula (112) 329 H CN General General H H H H H formula (112) formula (112) 330 H CN General General H H H CH₃ H formula (112) formula (112) 331 H CN General General H H H CH₃O H formula (112) formula (112) 332 General CN H H General H H H H formula (112) formula (112) 333 General CN H H General H H CH₃ H formula (112) formula (112) 334 General CN H H General H H CH₃O H formula (112) formula (112) 335 H CN General H General H H H H formula (112) formula (112) 336 H CN General H General H H CH₃ H formula (112) formula (112) 337 H CN General H General H H CH₃O H formula (112) formula (112) 338 H CN H General General H H H H formula (112) formula (112) 339 H CN H General General H H CH₃ H formula (112) formula (112) 340 H CN H General General H H CH₃O H formula (112) formula (112) 341 General CN H H H H H H H formula (112) 342 General CN H H H H H CH₃ H formula (112) 343 General CN H H H H H CH₃O H formula (112) 344 H CN General H H H H H H formula (112) 345 H CN General H H H H CH₃ H formula (112) 346 H CN General H H H H CH₃O H formula (112) 347 H CN H General H H H H H formula (112) 348 H CN H General H H H CH₃ H formula (112) 349 H CN H General H H H CH₃O H formula (112) 350 General CN General General F H H H H formula (112) formula (112) formula (112) 351 General CN General General F H H CH₃ H formula (112) formula (112) formula (112) 352 General CN General General F H H CH₃O H formula (112) formula (112) formula (112) 353 General CN General F General H H H H formula (112) formula (112) formula (112) 354 General CN General F General H H CH₃ H formula (112) formula (112) formula (112) 355 General CN General F General H H CH₃O H formula (112) formula (112) formula (112) 356 General CN F General General H H H H formula (112) formula (112) formula (112) 357 General CN F General General H H CH₃ H formula (112) formula (112) formula (112) 358 General CN F General General H H CH₃O H formula (112) formula (112) formula (112) 359 F CN General General General H H H H formula (112) formula (112) formula (112) 360 F CN General General General H H CH₃ H formula (112) formula (112) formula (112) 361 F CN General General General H H CH₃O H formula (112) formula (112) formula (112) 362 General CN General F F H H H H formula (112) formula (112) 363 General CN General F F H H CH₃ H formula (112) formula (112) 364 General CN General F F H H CH₃O H formula (112) formula (112) 365 General CN F General F H H H H formula (112) formula (112) 366 General CN F General F H H CH₃ H formula (112) formula (112) 367 General CN F General F H H CH₃O H formula (112) formula (112) 368 F CN General General F H H H H formula (112) formula (112) 369 F CN General General F H H CH₃ H formula (112) formula (112) 370 F CN General General F H H CH₃O H formula (112) formula (112) 371 General CN F F General H H H H formula (112) formula (112) 372 General CN F F General H H CH₃ H formula (112) formula (112) 373 General CN F F General H H CH₃O H formula (112) formula (112) 374 F CN General F General H H H H formula (112) formula (112) 375 F CN General F General H H CH₃ H formula (112) formula (112) 376 F CN General F General H H CH₃O H formula (112) formula (112) 377 F CN F General General H H H H formula (112) formula (112) 378 F CN F General General H H CH₃ H formula (112) formula (112) 379 F CN F General General H H CH₃O H formula (112) formula (112) 380 General CN F F F H H H H formula (112) 381 General CN F F F H H CH₃ H formula (112) 382 General CN F F F H H CH₃O H formula (112) 383 F CN General F F H H H H formula (112) 384 F CN General F F H H CH₃ H formula (112) 385 F CN General F F H H CH₃O H formula (112) 386 F CN F General F H H H H formula (112) 387 F CN F General F H H CH₃ H formula (112) 388 F CN F General F H H CH₃O H formula (112) 389 General CN General General OH H H H H formula (112) formula (112) formula (112) 390 General CN General General OH H H CH₃ H formula (112) formula (112) formula (112) 391 General CN General General OH H H CH₃O H formula (112) formula (112) formula (112) 392 General CN General OH General H H H H formula (112) formula (112) formula (112) 393 General CN General OH General H H CH H formula (112) formula (112) formula (112) 394 General CN General OH General H H CH₃O H formula (112) formula (112) formula (112) 395 General CN General OH General H H t-C₄H₉ H formula (112) formula (112) formula (112) 396 General CN General OH General H H Cl H formula (112) formula (112) formula (112) 397 General CN General OH General H H F H formula (112) formula (112) formula (112) 398 General CN OH General General H H H H formula (112) formula (112) formula (112) 399 General CN OH General General H H CH₃ H formula (112) formula (112) formula (112) 400 General CN OH General General H H CH₃O H formula (112) formula (112) formula (112) 401 OH CN General General General H H H H formula (112) formula (112) formula (112) 402 OH CN General General General H H CH₃ H formula (112) formula (112) formula (112) 403 OH CN General General General H H CH₃O H formula (112) formula (112) formula (112) 404 General CN General OH OH H H H H formula (112) formula (112) 405 General CN General OH OH H H CH₃ H formula (112) formula (112) 406 General CN General OH OH H H CH₃O H formula (112) formula (112) 407 General CN OH General OH H H H H formula (112) formula (112) 408 General CN OH General OH H H CH₃ H formula (112) formula (112) 409 General CN OH General OH H H CH₃O H formula (112) formula (112) 410 OH CN General General OH H H H H formula (112) formula (112) 411 OH CN General General OH H H CH₃ H formula (112) formula (112) 412 OH CN General General OH H H CH₃O H formula (112) formula (112) 413 General CN OH OH General H H H H formula (112) formula (112) 414 General CN OH OH General H H CH₃ H formula (112) formula (112) 415 General CN OH OH General H H CH₃O H formula (112) formula (112) 416 OH CN General OH General H H H H formula (112) formula (112) 417 OH CN General OH General H H CH₃ H formula (112) formula (112) 418 OH CN General OH General H H CH₃O H formula (112) formula (112) 419 OH CN OH General General H H H H formula (112) formula (112) 420 OH CN OH General General H H CH₃ H formula (112) formula (112) 421 OH CN OH General General H H CH₃O H formula (112) formula (112) 422 General CN OH OH OH H H H H formula (112) 423 General CN OH OH OH H H CH₃ H formula (112) 424 General CN OH OH OH H H CH₃O H formula (112) 425 OH CN General OH OH H H H H formula (112) 426 OH CN General OH OH H H CH₃ H formula (112) 427 OH CN General OH OH H H CH₃O H formula (112) 428 OH CN OH General OH H H H H formula (112) 429 OH CN OH General OH H H CH₃ H formula (112) 430 OH CN OH General OH H H CH₃O H formula (112) 431 OH CN OH OH General H H H H formula (112) 432 OH CN OH OH General H H CH₃ H formula (112) 433 OH CN OH OH General H H CH₃O H formula (112) 434 General CN General Cl General H H H H formula (112) formula (112) formula (112) 435 General CN General Cl General H H CH₃ H formula (112) formula (112) formula (112) 436 General CN General Cl General H H CH₃O H formula (112) formula (112) formula (112) 437 General CN General Cl General H H t-C₄H₉ H formula (112) formula (112) formula (112) 438 General CN General Cl General H H Cl H formula (112) formula (112) formula (112) 439 General CN General Cl General H H F H formula (112) formula (112) formula (112) 440 General CN General F General H H H H formula (112) formula (112) formula (112) 441 General CN General F General H H CH₃ H formula (112) formula (112) formula (112) 442 General CN General F General H H CH₃O H formula (112) formula (112) formula (112) 443 General CN General F General H H t-C₄H₉ H formula (112) formula (112) formula (112) 444 General CN General F General H H Cl H formula (112) formula (112) formula (112) 445 General CN General F General H H F H formula (112) formula (112) formula (112) 446 General CN General CH₃O General H H H H formula (112) formula (112) formula (112) 447 General CN General CH₃O General H H CH₃ H formula (112) formula (112) formula (112) 448 General CN General CH₃O General H H CH₃O H formula (112) formula (112) formula (112) 449 General CN General CH₃O General H H t-C₄H₉ H formula (112) formula (112) formula (112) 450 General CN General CH₃O General H H Cl H formula (112) formula (112) formula (112) 451 General CN General CH₃O General H H F H formula (112) formula (112) formula (112) 452 General CN General C₂H₅O General H H H H formula (112) formula (112) formula (112) 453 General CN General C₂H₅O General H H CH₃ H formula (112) formula (112) formula (112) 454 General CN General C₂H₅O General H H CH₃O H formula (112) formula (112) formula (112) 455 General CN General C₂H₅O General H H t-C₄H₉ H formula (112) formula (112) formula (112) 456 General CN General C₂H₅O General H H Cl H formula (112) formula (112) formula (112) 457 General CN General C₂H₅O General H H F H formula (112) formula (112) formula (112) 458 General CN General C₆H₅O General H H H H formula (112) formula (112) formula (112) 459 General CN General C₆H₅O General H H CH₃ H formula (112) formula (112) formula (112) 460 General CN General C₆H₅O General H H CH₃O H formula (112) formula (112) formula (112) 461 General CN General C₆H₅O General H H t-C₄H₉ H formula (112) formula (112) formula (112) 462 General CN General C₆H₅O General H H Cl H formula (112) formula (112) formula (112) 463 General CN General C₆H₅O General H H F H formula (112) formula (112) formula (112) 464 General CN General Formula General H H H H formula (112) formula (112) (121) formula (112) 465 General CN General Formula General H H CH₃ H formula (112) formula (112) (121) formula (112) 466 General CN General Formula General H H CH₃O H formula (112) formula (112) (121) formula (112) 467 General CN General Formula General H H t-C₄H₉ H formula (112) formula (112) (121) formula (112) 468 General CN General Formula General H H Cl H formula (112) formula (112) (121) formula (112) 469 General CN General Formula General H H F H formula (112) formula (112) (121) formula (112) 470 General CN General Formula General H H H H formula (112) formula (112) (122) formula (112) 471 General CN General Formula General H H CH₃ H formula (112) formula (112) (122) formula (112) 472 General CN General Formula General H H CH₃O H formula (112) formula (112) (122) formula (112) 473 General CN General Formula General H H t-C₄H₉ H formula (112) formula (112) (122) formula (112) 474 General CN General Formula General H H Cl H formula (112) formula (112) (122) formula (112) 475 General CN General Formula General H H F H formula (112) formula (112) (122) formula (112) 476 General CN General Formula General H H H H formula (112) formula (112) (123) formula (112) 477 General CN General Formula General H H CH₃ H formula (112) formula (112) (123) formula (112) 478 General CN General Formula General H H CH₃O H formula (112) formula (112) (123) formula (112) 479 General CN General Formula General H H t-C₄H₉ H formula (112) formula (112) (123) formula (112) 480 General CN General Formula General H H Cl H formula (112) formula (112) (123) formula (112) 481 General CN General Formula General H H F H formula (112) formula (112) (123) formula (112) 482 General CN General Formula General H H H H formula (112) formula (112) (124) formula (112) 483 General CN General Formula General H H CH₃ H formula (112) formula (112) (124) formula (112) 484 General CN General Formula General H H CH₃O H formula (112) formula (112) (124) formula (112) 485 General CN General Formula General H H t-C₄H₉ H formula (112) formula (112) (124) formula (112) 486 General CN General Formula General H H Cl H formula (112) formula (112) (124) formula (112) 487 General CN General Formula General H H F H formula (112) formula (112) (124) formula (112) 488 General CN General General General H C₆H₅ H H formula (112) formula (112) formula (112) formula (112) 489 General CN General General General H H C₆H₅ H formula (112) formula (112) formula (112) formula (112) 490 General CN General General H H C₆H₅ H H formula (112) formula (112) formula (112) 491 General CN General General H H H C₆H₅ H formula (112) formula (112) formula (112) 492 General CN General H General H C₆H₅ H H formula (112) formula (112) formula (112) 493 General CN General H General H H C₆H₅ H formula (112) formula (112) formula (112) 494 General CN H General General H C₆H₅ H H formula (112) formula (112) formula (112) 495 General CN H General General H H C₆H₅ H formula (112) formula (112) formula (112) 496 H CN General General General H C₆H₅ H H formula (112) formula (112) formula (112) 497 H CN General General General H H C₆H₅ H formula (112) formula (112) formula (112) 498 General CN General H H H C₆H₅ H H formula (112) formula (112) 499 General CN General H H H H C₆H₅ H formula (112) formula (112) 500-1 General CN H General H H C₆H₅ H H formula (112) formula (112) 500-2 General CN H General H H H C₆H₅ H formula (112) formula (112) 500-3 H CN General General H H C₆H₅ H H formula (112) formula (112) 500-4 H CN General General H H H C₆H₅ H formula (112) formula (112) 500-5 General CN H H General H C₆H₅ H H formula (112) formula (112) 500-6 General CN H H General H H C₆H₅ H formula (112) formula (112) 500-7 H CN General H General H C₆H₅ H H formula (112) formula (112) 500-8 H CN General H General H H C₆H₅ H formula (112) formula (112) 500-9 H CN H General General H C₆H₅ H H formula (112) formula (112) 500-10 H CN H General General H H C₆H₅ H formula (112) formula (112) 500-11 General CN H H H H C₆H₅ H H formula (112) 500-12 General CN H H H H H C₆H₅ H formula (112) 500-13 H CN General H H H C₆H₅ H H formula (112) 500-14 H CN General H H H H C₆H₅ H formula (112) 500-15 H CN H General H H C₆H₅ H H formula (112) 500-16 H CN H General H H H C₆H₅ H formula (112) 500-17 General CN General General F H H C₆H₅ H formula (112) formula (112) formula (112) 500-18 General CN General F General H H C₆H₅ H formula (112) formula (112) formula (112) 500-19 General CN F General General H H C₆H₅ H formula (112) formula (112) formula (112) 500-20 F CN General General General H H C₆H₅ H formula (112) formula (112) formula (112) 500-21 General CN General F F H H C₆H₅ H formula (112) formula (112) 500-22 General CN F General F H H C₆H₅ H formula (112) formula (112) 500-23 F CN General General F H H C₆H₅ H formula (112) formula (112) 500-24 General CN F F General H H C₆H₅ H formula (112) formula (112) 500-25 F CN General F General H H C₆H₅ H formula (112) formula (112) 500-26 F CN F General General H H C₆H₅ H formula (112) formula (112) 500-27 General CN F F F H H C₆H₅ H formula (112) 500-28 F CN General F F H H C₆H₅ H formula (112) 500-29 F CN F General F H H C₆H₅ H formula (112) 500-30 General CN General General OH H H C₆H₅ H formula (112) formula (112) formula (112) 500-31 General CN General OH General H H C₆H₅ H formula (112) formula (112) formula (112) 500-32 General CN OH General General H H C₆H₅ H formula (112) formula (112) formula (112) 500-33 OH CN General General General H H C₆H₅ H formula (112) formula (112) formula (112) 500-34 General CN General OH OH H H C₆H₅ H formula (112) formula (112) 500-35 General CN OH General OH H H C₆H₅ H formula (112) formula (112) 500-36 OH CN General General OH H H C₆H₅ H formula (112) formula (112) 500-37 General CN OH OH General H H C₆H₅ H formula (112) formula (112) 500-38 OH CN General OH General H H C₆H₅ H formula (112) formula (112) 500-39 OH CN OH General General H H C₆H₅ H formula (112) formula (112) 500-40 General CN OH OH OH H H C₆H₅ H formula (112) 500-41 OH CN General OH OH H H C₆H₅ H formula (112) 500-42 OH CN OH General OH H H C₆H₅ H formula (112) 500-43 OH CN OH OH General H H C₆H₅ H formula (112) 500-44 General CN General Cl General H H C₆H₅ H formula (112) formula (112) formula (112) 500-45 General CN General F General H H C₆H₅ H formula (112) formula (112) formula (112) 500-46 General CN General CH₃O General H H C₆H₅ H formula (112) formula (112) formula (112) 500-47 General CN General C₂H₅O General H H C₆H₅ H formula (112) formula (112) formula (112) 500-48 General CN General C₆H₅O General H H C₆H₅ H formula (112) formula (112) formula (112) 500-49 General CN General Formula General H H C₆H₅ H formula (112) formula (112) (121) formula (112) 500-50 General CN General Formula General H H C₆H₅ H formula (112) formula (112) (122) formula (112) 500-51 General CN General Formula General H H C₆H₅ H formula (112) formula (112) (123) formula (112) 500-52 General CN General Formula General H H C₆H₅ H formula (112) formula (112) (124) formula (112)

TABLE 3 Compound General formula (101) General formula (112) No. R¹ R² R³ R⁴ R⁵ R³¹, R³⁸ R³², R³⁷ R³³, R³⁶ R³⁴, R³⁵ 501 CN General General General General H H H H formula (112) formula (112) formula (112) formula (112) 502 CN General General General General H CH₃ H H formula (112) formula (112) formula (112) formula (112) 503 CN General General General General H CH₃O H H formula (112) formula (112) formula (112) formula (112) 504 CN General General General General H H CH₃ H formula (112) formula (112) formula (112) formula (112) 505 CN General General General General H H CH₃O H formula (112) formula (112) formula (112) formula (112) 506 CN General General General General H H t-C₄H₉ H formula (112) formula (112) formula (112) formula (112) 507 CN General General General General H H Cl H formula (112) formula (112) formula (112) formula (112) 508 CN General General General General H H F H formula (112) formula (112) formula (112) formula (112) 509 CN General General General General H H H CH₃ formula (112) formula (112) formula (112) formula (112) 510 CN General General General General H H H CH₃O formula (112) formula (112) formula (112) formula (112) 511 CN General General General H H H H H formula (112) formula (112) formula (112) 512 CN General General General H H H CH₃ H formula (112) formula (112) formula (112) 513 CN General General General H H H CH₃O H formula (112) formula (112) formula (112) 514 CN General General H General H H H H formula (112) formula (112) formula (112) 515 CN General General H General H H CH₃ H formula (112) formula (112) formula (112) 516 CN General General H General H H CH₃O H formula (112) formula (112) formula (112) 517 CN General General H H H H H H formula (112) formula (112) 518 CN General General H H H H CH₃ H formula (112) formula (112) 519 CN General General H H H H CH₃O H formula (112) formula (112) 520 CN General H General H H H H H formula (112) formula (112) 521 CN General H General H H H CH₃ H formula (112) formula (112) 522 CN General H General H H H CH₃O H formula (112) formula (112) 523 CN H General General H H H H H formula (112) formula (112) 524 CN H General General H H H CH₃ H formula (112) formula (112) 525 CN H General General H H H CH₃O H formula (112) formula (112) 526 CN General H H General H H H H formula (112) formula (112) 527 CN General H H General H H CH₃ H formula (112) formula (112) 528 CN General H H General H H CH₃O H formula (112) formula (112) 529 CN General H H H H H H H formula (112) 530 CN General H H H H H CH₃ H formula (112) 531 CN General H H H H H CH₃O H formula (112) 532 CN H General H H H H H H formula (112) 533 CN H General H H H H CH₃ H formula (112) 534 CN H General H H H H CH₃O H formula (112) 535 CN General General General F H H H H formula (112) formula (112) formula (112) 536 CN General General General F H H CH₃ H formula (112) formula (112) formula (112) 537 CN General General General F H H CH₃O H formula (112) formula (112) formula (112) 538 CN General General F General H H H H formula (112) formula (112) formula (112) 539 CN General General F General H H CH₃ H formula (112) formula (112) formula (112) 540 CN General General F General H H CH₃O H formula (112) formula (112) formula (112) 541 CN General General F F H H H H formula (112) formula (112) 542 CN General General F F H H CH₃ H formula (112) formula (112) 543 CN General General F F H H CH₃O H formula (112) formula (112) 544 CN General F General F H H H H formula (112) formula (112) 545 CN General F General F H H CH₃ H formula (112) formula (112) 546 CN General F General F H H CH₃O H formula (112) formula (112) 547 CN F General General F H H H H formula (112) formula (112) 548 CN F General General F H H CH₃ H formula (112) formula (112) 549 CN F General General F H H CH₃O H formula (112) formula (112) 550 CN General F F General H H H H formula (112) formula (112) 551 CN General F F General H H CH₃ H formula (112) formula (112) 552 CN General F F General H H CH₃O H formula (112) formula (112) 553 CN General F F F H H H H formula (112) 554 CN General F F F H H CH₃ H formula (112) 555 CN General F F F H H CH₃O H formula (112) 556 CN F General F F H H H H formula (112) 557 CN F General F F H H CH₃ H formula (112) 558 CN F General F F H H CH₃O H formula (112) 559 CN General General General OH H H H H formula (112) formula (112) formula (112) 560 CN General General General OH H H CH₃ H formula (112) formula (112) formula (112) 561 CN General General General OH H H CH₃O H formula (112) formula (112) formula (112) 562 CN General General OH General H H H H formula (112) formula (112) formula (112) 563 CN General General OH General H H CH₃ H formula (112) formula (112) formula (112) 654 CN General General OH General H H CH₃O H formula (112) formula (112) formula (112) 565 CN General General OH General H H Cl H formula (112) formula (112) formula (112) 566 CN General General OH General H H F H formula (112) formula (112) formula (112) 567 CN General General OH OH H H H H formula (112) formula (112) 568 CN General General OH OH H H CH₃ H formula (112) formula (112) 569 CN General General OH OH H H CH₃O H formula (112) formula (112) 570 CN General OH General OH H H H H formula (112) formula (112) 571 CN General OH General OH H H CH₃ H formula (112) formula (112) 572 CN General OH General OH H H CH₃O H formula (112) formula (112) 573 CN OH General General OH H H H H formula (112) formula (112) 574 CN OH General General OH H H CH₃ H formula (112) formula (112) 575 CN OH General General OH H H CH₃O H formula (112) formula (112) 576 CN General OH OH General H H H H formula (112) formula (112) 577 CN General OH OH General H H CH₃ H formula (112) formula (112) 578 CN General OH OH General H H CH₃O H formula (112) formula (112) 579 CN General OH OH OH H H H H formula (112) 580 CN General OH OH OH H H CH₃ H formula (112) 581 CN General OH OH OH H H CH₃O H formula (112) 582 CN OH General OH OH H H H H formula (112) 583 CN OH General OH OH H H CH₃ H formula (112) 584 CN OH General OH OH H H CH₃O H formula (112) 585 CN General General Cl General H H H H formula (112) formula (112) formula (112) 586 CN General General Cl General H H CH₃ H formula (112) formula (112) formula (112) 587 CN General General Cl General H H CH₃O H formula (112) formula (112) formula (112) 588 CN General General Cl General H H t-C₄H₉ H formula (112) formula (112) formula (112) 589 CN General General Cl General H H Cl H formula (112) formula (112) formula (112) 590 CN General General Cl General H H F H formula (112) formula (112) formula (112) 591 CN General General F General H H H H formula (112) formula (112) formula (112) 592 CN General General F General H H CH₃ H formula (112) formula (112) formula (112) 593 CN General General F General H H CH₃O H formula (112) formula (112) formula (112) 594 CN General General F General H H t-C₄H₉ H formula (112) formula (112) formula (112) 595 CN General General F General H H Cl H formula (112) formula (112) formula (112) 596 CN General General F General H H F H formula (112) formula (112) formula (112) 597 CN General General CH₃O General H H H H formula (112) formula (112) formula (112) 598 CN General General CH₃O General H H CH₃ H formula (112) formula (112) formula (112) 599 CN General General CH₃O General H H CH₃O H formula (112) formula (112) formula (112) 600 CN General General CH₃O General H H t-C₄H₉ H formula (112) formula (112) formula (112) 601 CN General General CH₃O General H H Cl H formula (112) formula (112) formula (112) 602 CN General General CH₃O General H H F H formula (112) formula (112) formula (112) 603 CN General General C₂H₅O General H H H H formula (112) formula (112) formula (112) 604 CN General General C₂H₅O General H H CH₃ H formula (112) formula (112) formula (112) 605 CN General General C₂H₅O General H H CH₃O H formula (112) formula (112) formula (112) 606 CN General General C₂H₅O General H H t-C₄H₉ H formula (112) formula (112) formula (112) 607 CN General General C₂H₅O General H H Cl H formula (112) formula (112) formula (112) 608 CN General General C₂H₅O General H H F H formula (112) formula (112) formula (112) 609 CN General General C₆H₅O General H H H H formula (112) formula (112) formula (112) 610 CN General General C₆H₅O General H H CH₃ H formula (112) formula (112) formula (112) 611 CN General General C₆H₅O General H H CH₃O H formula (112) formula (112) formula (112) 612 CN General General C₆H₅O General H H t-C₄H₉ H formula (112) formula (112) formula (112) 613 CN General General C₆H₅O General H H Cl H formula (112) formula (112) formula (112) 614 CN General General C₆H₅O General H H F H formula (112) formula (112) formula (112) 615 CN General General Formula General H H H H formula (112) formula (112) (121) formula (112) 616 CN General General Formula General H H CH₃ H formula (112) formula (112) (121) formula (112) 617 CN General General Formula General H H CH₃O H formula (112) formula (112) (121) formula (112) 618 CN General General Formula General H H t-C₄H₉ H formula (112) formula (112) (121) formula (112) 619 CN General General Formula General H H Cl H formula (112) formula (112) (121) formula (112) 620 CN General General Formula General H H F H formula (112) formula (112) (121) formula (112) 621 CN General General Formula General H H H H formula (112) formula (112) (122) formula (112) 622 CN General General Formula General H H CH₃ H formula (112) formula (112) (122) formula (112) 623 CN General General Formula General H H CH₃O H formula (112) formula (112) (122) formula (112) 624 CN General General Formula General H H t-C₄H₉ H formula (112) formula (112) (122) formula (112) 625 CN General General Formula General H H Cl H formula (112) formula (112) (122) formula (112) 626 CN General General Formula General H H F H formula (112) formula (112) (122) formula (112) 627 CN General General Formula General H H H H formula (112) formula (112) (123) formula (112) 628 CN General General Formula General H H CH₃ H formula (112) formula (112) (123) formula (112) 629 CN General General Formula General H H CH₃O H formula (112) formula (112) (123) formula (112) 630 CN General General Formula General H H t-C₄H₉ H formula (112) formula (112) (123) formula (112) 631 CN General General Formula General H H Cl H formula (112) formula (112) (123) formula (112) 632 CN General General Formula General H H F H formula (112) formula (112) (123) formula (112) 633 CN General General Formula General H H H H formula (112) formula (112) (124) formula (112) 634 CN General General Formula General H H CH₃ H formula (112) formula (112) (124) formula (112) 635 CN General General Formula General H H CH₃O H formula (112) formula (112) (124) formula (112) 636 CN General General Formula General H H t-C₄H₉ H formula (112) formula (112) (124) formula (112) 637 CN General General Formula General H H Cl H formula (112) formula (112) (124) formula (112) 638 CN General General Formula General H H F H formula (112) formula (112) (124) formula (112) 639 CN General General General General H C₆H₅ H H formula (112) formula (112) formula (112) formula (112) 640 CN General General General General H H C₆H₅ H formula (112) formula (112) formula (112) formula (112) 641 CN General General General H H C₆H₅ H H formula (112) formula (112) formula (112) 642 CN General General General H H H C₆H₅ H formula (112) formula (112) formula (112) 643 CN General General H General H C₆H₅ H H formula (112) formula (112) formula (112) 644 CN General General H General H H C₆H₅ H formula (112) formula (112) formula (112) 645 CN General General H H H C₆H₅ H H formula (112) formula (112) 646 CN General General H H H H C₆H₅ H formula (112) formula (112) 647 CN General H General H H C₆H₅ H H formula (112) formula (112) 648 CN General H General H H H C₆H₅ H formula (112) formula (112) 649 CN H General General H H C₆H₅ H H formula (112) formula (112) 650 CN H General General H H H C₆H₅ H formula (112) formula (112) 651 CN H H General General H C₆H₅ H H formula (112) formula (112) 652 CN H H General General H H C₆H₅ H formula (112) formula (112) 653 CN General H H H H C₆H₅ H H formula (112) 654 CN General H H H H H C₆H₅ H formula (112) 655 CN H General H H H C₆H₅ H H formula (112) 656 CN H General H H H H C₆H₅ H formula (112) 657 CN General General General F H H C₆H₅ H formula (112) formula (112) formula (112) 658 CN General General F General H H C₆H₅ H formula (112) formula (112) formula (112) 659 CN General General F F H H C₆H₅ H formula (112) formula (112) 660 CN General F General F H H C₆H₅ H formula (112) formula (112) 661 CN F General General F H H C₆H₅ H formula (112) formula (112) 662 CN F F General General H H C₆H₅ H formula (112) formula (112) 663 CN General F F F H H C₆H₅ H formula (112) 664 CN F General F F H H C₆H₅ H formula (112) 665 CN General General General OH H H C₆H₅ H formula (112) formula (112) formula (112) 666 CN General General OH General H H C₆H₅ H formula (112) formula (112) formula (112) 667 CN General General OH OH H H C₆H₅ H formula (112) formula (112) 668 CN General OH General OH H H C₆H₅ H formula (112) formula (112) 669 CN OH General General OH H H C₆H₅ H formula (112) formula (112) 670 CN OH OH General General H H C₆H₅ H formula (112) formula (112) 671 CN General OH OH OH H H C₆H₅ H formula (112) 672 CN OH General OH OH H H C₆H₅ H formula (112) 673 CN General General Cl General H H C₆H₅ H formula (112) formula (112) formula (112) 674 CN General General F General H H C₆H₅ H formula (112) formula (112) formula (112) 675 CN General General CH₃O General H H C₆H₅ H formula (112) formula (112) formula (112) 676 CN General General C₂H₅O General H H C₆H₅ H formula (112) formula (112) formula (112) 677 CN General General C₆H₅O General H H C₆H₅ H formula (112) formula (112) formula (112) 678 CN General General Formula General H H C₆H₅ H formula (112) formula (112) (121) formula (112) 679 CN General General Formula General H H C₆H₅ H formula (112) formula (112) (122) formula (112) 680 CN General General Formula General H H C₆H₅ H formula (112) formula (112) (123) formula (112) 681 CN General General Formula General H H C₆H₅ H formula (112) formula (112) (124) formula (112)

TABLE 4 Compound General formula (101) No. R¹ R² R³ R⁴ R⁵ 701 General formula (113) General formula (113) CN General formula (113) General formula (113) 702 General formula (113) General formula (113) CN General formula (113) General formula (113) 703 General formula (113) General formula (113) CN General formula (113) General formula (113) 704 General formula (113) General formula (113) CN General formula (113) General formula (113) 705 General formula (113) General formula (113) CN General formula (113) General formula (113) 706 General formula (113) General formula (113) CN General formula (113) General formula (113) 707 General formula (113) General formula (113) CN General formula (113) General formula (113) 708 General formula (113) General formula (113) CN General formula (113) General formula (113) 709 General formula (113) General formula (113) CN General formula (113) General formula (113) 710 General formula (113) General formula (113) CN General formula (113) General formula (113) 711 General formula (113) General formula (113) CN General formula (113) General formula (113) 712 General formula (113) General formula (113) CN General formula (113) General formula (113) 713 General formula (113) General formula (113) CN General formula (113) General formula (113) 714 General formula (113) General formula (113) CN General formula (113) General formula (113) 715 General formula (113) General formula (113) CN General formula (113) General formula (113) 716 General formula (113) General formula (113) CN General formula (113) General formula (113) 717 General formula (113) General formula (113) CN General formula (113) General formula (113) 718 General formula (113) General formula (113) CN General formula (113) General formula (113) 719 General formula (113) General formula (113) CN General formula (113) General formula (113) 720 General formula (113) General formula (113) CN General formula (113) General formula (113) 721 General formula (113) General formula (113) CN General formula (113) General formula (113) 722 General formula (113) General formula (113) CN General formula (113) General formula (113) 723 General formula (113) General formula (113) CN General formula (113) General formula (113) 724 General formula (113) General formula (113) CN General formula (113) General formula (113) 725 General formula (113) General formula (113) CN General formula (113) General formula (113) 726 General formula (113) General formula (113) CN General formula (113) General formula (113) 727 General formula (113) General formula (113) CN General formula (113) General formula (113) 728 General formula (113) General formula (113) CN General formula (113) General formula (113) 729 General formula (113) General formula (113) CN General formula (113) General formula (113) 730 General formula (113) General formula (113) CN General formula (113) General formula (113) 731 General formula (113) General formula (113) CN General formula (113) General formula (113) 732 General formula (113) General formula (113) CN General formula (113) General formula (113) 733 General formula (113) General formula (113) CN General formula (113) General formula (113) 734 General formula (113) General formula (113) CN General formula (113) General formula (113) 735 General formula (113) General formula (113) CN General formula (113) H 736 General formula (113) General formula (113) CN H General formula (113) 737 General formula (113) General formula (113) CN H H 738 General formula (113) H CN General formula (113) H 739 H General formula (113) CN General formula (113) H 740 General formula (113) H CN H H 741 General formula (113) General formula (113) CN General formula (113) F 742 General formula (113) General formula (113) CN F General formula (113) 743 General formula (113) General formula (113) CN F F 744 General formula (113) F CN General formula (113) F 745 F General formula (113) CN General formula (113) F 746 General formula (113) F CN F F 747 General formula (113) General formula (113) CN General formula (113) OH 748 General formula (113) General formula (113) CN OH General formula (113) 749 General formula (113) General formula (113) CN OH OH 750 General formula (113) OH CN General formula (113) OH 751 OH General formula (113) CN General formula (113) OH 752 General formula (113) OH CN OH OH 753 General formula (113) General formula (113) CN Cl General formula (113) 754 General formula (113) General formula (113) CN Cl General formula (113) 755 General formula (113) General formula (113) CN Cl General formula (113) 756 General formula (113) General formula (113) CN Cl General formula (113) 757 General formula (113) General formula (113) CN Cl General formula (113) 758 General formula (113) General formula (113) CN Cl General formula (113) 759 General formula (113) General formula (113) CN F General formula (113) 760 General formula (113) General formula (113) CN F General formula (113) 761 General formula (113) General formula (113) CN F General formula (113) 762 General formula (113) General formula (113) CN F General formula (113) 763 General formula (113) General formula (113) CN F General formula (113) 764 General formula (113) General formula (113) CN F General formula (113) 765 General formula (113) General formula (113) CN CH₃O General formula (113) 766 General formula (113) General formula (113) CN CH₃O General formula (113) 767 General formula (113) General formula (113) CN CH₃O General formula (113) 768 General formula (113) General formula (113) CN CH₃O General formula (113) 769 General formula (113) General formula (113) CN CH₃O General formula (113) 770 General formula (113) General formula (113) CN CH₃O General formula (113) 771 General formula (113) General formula (113) CN C₂H₅O General formula (113) 772 General formula (113) General formula (113) CN C₂H₅O General formula (113) 773 General formula (113) General formula (113) CN C₂H₅O General formula (113) 774 General formula (113) General formula (113) CN C₂H₅O General formula (113) 775 General formula (113) General formula (113) CN C₂H₅O General formula (113) 776 General formula (113) General formula (113) CN C₂H₅O General formula (113) 777 General formula (113) General formula (113) CN C₆H₅O General formula (113) 778 General formula (113) General formula (113) CN C₆H₅O General formula (113) 779 General formula (113) General formula (113) CN C₆H₅O General formula (113) 780 General formula (113) General formula (113) CN C₆H₅O General formula (113) 781 General formula (113) General formula (113) CN C₆H₅O General formula (113) 782 General formula (113) General formula (113) CN C₆H₅O General formula (113) 783 General formula (113) General formula (113) CN Formula (121) General formula (113) 784 General formula (113) General formula (113) CN Formula (121) General formula (113) 785 General formula (113) General formula (113) CN Formula (121) General formula (113) 786 General formula (113) General formula (113) CN Formula (121) General formula (113) 787 General formula (113) General formula (113) CN Formula (121) General formula (113) 788 General formula (113) General formula (113) CN Formula (121) General formula (113) 789 General formula (113) General formula (113) CN Formula (122) General formula (113) 790 General formula (113) General formula (113) CN Formula (122) General formula (113) 791 General formula (113) General formula (113) CN Formula (122) General formula (113) 792 General formula (113) General formula (113) CN Formula (122) General formula (113) 793 General formula (113) General formula (113) CN Formula (122) General formula (113) 794 General formula (113) General formula (113) CN Formula (122) General formula (113) 795 General formula (113) General formula (113) CN Formula (123) General formula (113) 796 General formula (113) General formula (113) CN Formula (123) General formula (113) 797 General formula (113) General formula (113) CN Formula (123) General formula (113) 798 General formula (113) General formula (113) CN Formula (123) General formula (113) 799 General formula (113) General formula (113) CN Formula (123) General formula (113) 800 General formula (113) General formula (113) CN Formula (123) General formula (113) 801 General formula (113) General formula (113) CN Formula (124) General formula (113) 802 General formula (113) General formula (113) CN Formula (124) General formula (113) 803 General formula (113) General formula (113) CN Formula (124) General formula (113) 804 General formula (113) General formula (113) CN Formula (124) General formula (113) 805 General formula (113) General formula (113) CN Formula (124) General formula (113) 806 General formula (113) General formula (113) CN Formula (124) General formula (113) Compound General formula (113) No. R⁴¹ R⁴² R⁴³ R⁴⁴ R⁴⁵ R⁴⁶ 701 H H H H H H 702 H CH₃ H H H H 703 H CH₃O H H H H 704 H H CH₃ H H H 705 H H CH₃O H H H 706 H H t-C₄H₉ H H H 707 H H Cl H H H 708 H H F H H H 709 H H H CH₃ H H 710 H H H CH₃O H H 711 H H H H CH₃ H 712 H H H H CH₃O H 713 H H H H t-C₄H₉ H 714 H H H H Cl H 715 H H H H F H 716 H H H H C₆H₅ H 717 H H H H p-CH₃C₆H₄ H 718 H H H H 2,4,6-(CH₃)₃C₆H₂ H 719 H H H H p-CH₃OC₆H₄ H 720 H H H H p-(CH₃)₂NC₆H₄ H 721 H H H H p-FC₆H₄ H 722 H H H H p-CNC₆H₄ H 723 H H H H H CH₃ 724 H H H H H CH₃O 725 H H H H H t-C₄H₉ 726 H H H H H Cl 727 H H H H H F 728 H H H H H C₆H₅ 729 H H H H H p-CH₃C₆H₄ 730 H H H H H 2,4,6-(CH₃)₃C₆H₂ 731 H H H H H p-CH₃OC₆H₄ 732 H H H H H p-(CH₃)₂NC₆H₄ 733 H H H H H p-FC₆H₄ 734 H H H H H p-CNC₆H₄ 735 H H H H H H 736 H H H H H H 737 H H H H H H 738 H H H H H H 739 H H H H H H 740 H H H H H H 741 H H H H H H 742 H H H H H H 743 H H H H H H 744 H H H H H H 745 H H H H H H 746 H H H H H H 747 H H H H H H 748 H H H H H H 749 H H H H H H 750 H H H H H H 751 H H H H H H 752 H H H H H H 753 H H H H H H 754 H H CH₃ H H H 755 H H CH₃O H H H 756 H H t-C₄H₉ H H H 757 H H Cl H H H 758 H H F H H H 759 H H H H H H 760 H H CH₃ H H H 761 H H CH₃O H H H 762 H H t-C₄H₉ H H H 763 H H Cl H H H 764 H H F H H H 765 H H H H H H 766 H H CH₃ H H H 767 H H CH₃O H H H 768 H H t-C₄H₉ H H H 769 H H Cl H H H 770 H H F H H H 771 H H H H H H 772 H H CH₃ H H H 773 H H CH₃O H H H 774 H H t-C₄H₉ H H H 775 H H Cl H H H 776 H H F H H H 777 H H H H H H 778 H H CH₃ H H H 779 H H CH₃O H H H 780 H H t-C₄H₉ H H H 781 H H Cl H H H 782 H H F H H H 783 H H H H H H 784 H H CH₃ H H H 785 H H CH₃O H H H 786 H H t-C₄H₉ H H H 787 H H Cl H H H 788 H H F H H H 789 H H H H H H 790 H H CH₃ H H H 791 H H CH₃O H H H 792 H H t-C₄H₉ H H H 793 H H Cl H H H 794 H H F H H H 795 H H H H H H 796 H H CH₃ H H H 797 H H CH₃O H H H 798 H H t-C₄H₉ H H H 799 H H Cl H H H 800 H H F H H H 801 H H H H H H 802 H H CH₃ H H H 803 H H CH₃O H H H 804 H H t-C₄H₉ H H H 805 H H Cl H H H 806 H H F H H H

TABLE 5 Compound General formula (101) No. R¹ R² R³ R⁴ R⁵ 901 General formula (114) General formula (114) CN General formula (114) General formula (114) 902 General formula (114) General formula (114) CN General formula (114) General formula (114) 903 General formula (114) General formula (114) CN General formula (114) General formula (114) 904 General formula (114) General formula (114) CN General formula (114) General formula (114) 905 General formula (114) General formula (114) CN General formula (114) General formula (114) 906 General formula (114) General formula (114) CN General formula (114) General formula (114) 907 General formula (114) General formula (114) CN General formula (114) General formula (114) 908 General formula (114) General formula (114) CN General formula (114) General formula (114) 909 General formula (114) General formula (114) CN General formula (114) General formula (114) 910 General formula (114) General formula (114) CN General formula (114) General formula (114) 911 General formula (114) General formula (114) CN General formula (114) General formula (114) 912 General formula (114) General formula (114) CN General formula (114) General formula (114) 913 General formula (114) General formula (114) CN General formula (114) General formula (114) 914 General formula (114) General formula (114) CN General formula (114) General formula (114) 915 General formula (114) General formula (114) CN General formula (114) General formula (114) 916 General formula (114) General formula (114) CN General formula (114) General formula (114) 917 General formula (114) General formula (114) CN General formula (114) General formula (114) 918 General formula (114) General formula (114) CN General formula (114) General formula (114) 919 General formula (114) General formula (114) CN General formula (114) H 920 General formula (114) General formula (114) CN H General formula (114) 921 General formula (114) General formula (114) CN H H 922 General formula (114) H CN General formula (114) H 923 H General formula (114) CN General formula (114) H 924 General formula (114) H CN H H 925 General formula (114) General formula (114) CN General formula (114) F 926 General formula (114) General formula (114) CN F General formula (114) 927 General formula (114) General formula (114) CN F F 928 General formula (114) F CN General formula (114) F 929 F General formula (114) CN General formula (114) F 930 General formula (114) F CN F F 931 General formula (114) General formula (114) CN General formula (114) OH 932 General formula (114) General formula (114) CN OH General formula (114) 933 General formula (114) General formula (114) CN OH OH 934 General formula (114) OH CN General formula (114) OH 935 OH General formula (114) CN General formula (114) OH 936 General formula (114) OH CN OH OH 937 General formula (114) General formula (114) CN Cl General formula (114) 938 General formula (114) General formula (114) CN Cl General formula (114) 939 General formula (114) General formula (114) CN Cl General formula (114) 940 General formula (114) General formula (114) CN Cl General formula (114) 941 General formula (114) General formula (114) CN Cl General formula (114) 942 General formula (114) General formula (114) CN Cl General formula (114) 943 General formula (114) General formula (114) CN F General formula (114) 944 General formula (114) General formula (114) CN F General formula (114) 945 General formula (114) General formula (114) CN F General formula (114) 946 General formula (114) General formula (114) CN F General formula (114) 947 General formula (114) General formula (114) CN F General formula (114) 948 General formula (114) General formula (114) CN F General formula (114) 949 General formula (114) General formula (114) CN CH₃O General formula (114) 950 General formula (114) General formula (114) CN CH₃O General formula (114) 951 General formula (114) General formula (114) CN CH₃O General formula (114) 952 General formula (114) General formula (114) CN CH₃O General formula (114) 953 General formula (114) General formula (114) CN CH₃O General formula (114) 954 General formula (114) General formula (114) CN CH₃O General formula (114) 955 General formula (114) General formula (114) CN C₂H₅O General formula (114) 956 General formula (114) General formula (114) CN C₂H₅O General formula (114) 957 General formula (114) General formula (114) CN C₂H₅O General formula (114) 958 General formula (114) General formula (114) CN C₂H₅O General formula (114) 959 General formula (114) General formula (114) CN C₂H₅O General formula (114) 960 General formula (114) General formula (114) CN C₂H₅O General formula (114) 961 General formula (114) General formula (114) CN C₆H₅O General formula (114) 962 General formula (114) General formula (114) CN C₆H₅O General formula (114) 963 General formula (114) General formula (114) CN C₆H₅O General formula (114) 964 General formula (114) General formula (114) CN C₆H₅O General formula (114) 965 General formula (114) General formula (114) CN C₆H₅O General formula (114) 966 General formula (114) General formula (114) CN C₆H₅O General formula (114) 967 General formula (114) General formula (114) CN Formula (121) General formula (114) 968 General formula (114) General formula (114) CN Formula (121) General formula (114) 969 General formula (114) General formula (114) CN Formula (121) General formula (114) 970 General formula (114) General formula (114) CN Formula (121) General formula (114) 971 General formula (114) General formula (114) CN Formula (121) General formula (114) 972 General formula (114) General formula (114) CN Formula (121) General formula (114) 973 General formula (114) General formula (114) CN Formula (122) General formula (114) 974 General formula (114) General formula (114) CN Formula (122) General formula (114) 975 General formula (114) General formula (114) CN Formula (122) General formula (114) 976 General formula (114) General formula (114) CN Formula (122) General formula (114) 977 General formula (114) General formula (114) CN Formula (122) General formula (114) 978 General formula (114) General formula (114) CN Formula (122) General formula (114) 989 General formula (114) General formula (114) CN Formula (123) General formula (114) 980 General formula (114) General formula (114) CN Formula (123) General formula (114) 981 General formula (114) General formula (114) CN Formula (123) General formula (114) 982 General formula (114) General formula (114) CN Formula (123) General formula (114) 983 General formula (114) General formula (114) CN Formula (123) General formula (114) 984 General formula (114) General formula (114) CN Formula (123) General formula (114) 985 General formula (114) General formula (114) CN Formula (124) General formula (114) 986 General formula (114) General formula (114) CN Formula (124) General formula (114) 987 General formula (114) General formula (114) CN Formula (124) General formula (114) 988 General formula (114) General formula (114) CN Formula (124) General formula (114) 989 General formula (114) General formula (114) CN Formula (124) General formula (114) 990 General formula (114) General formula (114) CN Formula (124) General formula (114) General formula (113) Compound R⁵¹, R⁵⁶, No. R⁵² R⁵³ R⁵⁴ R⁵⁵ R⁵⁷ R⁵⁹ R⁶¹ R⁵⁸, R⁶⁰, R⁶² 901 H H H H H H H H 902 CH₃ H H H H H H H 903 CH₃O H H H H H H H 904 H CH₃ H H H H H H 905 H CH₃O H H H H H H 906 H t-C₄H₉ H H H H H H 907 H Cl H H H H H H 908 H F H H H H H H 909 H H CH₃ H H H H H 910 H H CH₃O H H H H H 911 H H H CH₃ H H H H 912 H H H CH₃O H H H H 913 H H H H CH₃ H H H 914 H H H H CH₃O H H H 915 H H H H H CH₃ H H 916 H H H H H CH₃O H H 917 H H H H H H CH₃ H 918 H H H H H H CH₃O H 919 H H H H H H H H 920 H H H H H H H H 921 H H H H H H H H 922 H H H H H H H H 923 H H H H H H H H 924 H H H H H H H H 925 H H H H H H H H 926 H H H H H H H H 927 H H H H H H H H 928 H H H H H H H H 929 H H H H H H H H 930 H H H H H H H H 931 H H H H H H H H 932 H H H H H H H H 933 H H H H H H H H 934 H H H H H H H H 935 H H H H H H H H 936 H H H H H H H H 937 H H H H H H H H 938 H CH₃ H H H H H H 939 H CH₃O H H H H H H 940 H t-C₄H₉ H H H H H H 941 H Cl H H H H H H 942 H F H H H H H H 943 H H H H H H H H 944 H CH₃ H H H H H H 945 H CH₃O H H H H H H 946 H t-C₄H₉ H H H H H H 947 H Cl H H H H H H 948 H F H H H H H H 949 H H H H H H H H 950 H CH₃ H H H H H H 951 H CH₃O H H H H H H 952 H t-C₄H₉ H H H H H H 953 H Cl H H H H H H 954 H F H H H H H H 955 H H H H H H H H 956 H CH₃ H H H H H H 957 H CH₃O H H H H H H 958 H t-C₄H₉ H H H H H H 959 H Cl H H H H H H 960 H F H H H H H H 961 H H H H H H H H 962 H CH₃ H H H H H H 963 H CH₃O H H H H H H 964 H t-C₄H₉ H H H H H H 965 H Cl H H H H H H 966 H F H H H H H H 967 H H H H H H H H 968 H CH₃ H H H H H H 969 H CH₃O H H H H H H 970 H t-C₄H₉ H H H H H H 971 H Cl H H H H H H 972 H F H H H H H H 973 H H H H H H H H 974 H CH₃ H H H H H H 975 H CH₃O H H H H H H 976 H t-C₄H₉ H H H H H H 977 H Cl H H H H H H 978 H F H H H H H H 989 H H H H H H H H 980 H CH₃ H H H H H H 981 H CH₃O H H H H H H 982 H t-C₄H₉ H H H H H H 983 H Cl H H H H H H 984 H F H H H H H H 985 H H H H H H H H 986 H CH₃ H H H H H H 987 H CH₃O H H H H H H 988 H t-C₄H₉ H H H H H H 989 H Cl H H H H H H 990 H F H H H H H H

TABLE 6 Compound General formula (101) No. R¹ R² R³ R⁴ R⁵ 1001 General formula (115) General formula (115) CN General formula (115) General formula (115) 1002 General formula (115) General formula (115) CN General formula (115) General formula (115) 1003 General formula (115) General formula (115) CN General formula (115) General formula (115) 1004 General formula (115) General formula (115) CN General formula (115) General formula (115) 1005 General formula (115) General formula (115) CN General formula (115) General formula (115) 1006 General formula (115) General formula (115) CN General formula (115) General formula (115) 1007 General formula (115) General formula (115) CN General formula (115) General formula (115) 1008 General formula (115) General formula (115) CN General formula (115) General formula (115) 1009 General formula (115) General formula (115) CN General formula (115) General formula (115) 1010 General formula (115) General formula (115) CN General formula (115) General formula (115) 1011 General formula (115) General formula (115) CN General formula (115) General formula (115) 1012 General formula (115) General formula (115) CN General formula (115) General formula (115) 1013 General formula (115) General formula (115) CN General formula (115) General formula (115) 1014 General formula (115) General formula (115) CN General formula (115) General formula (115) 1015 General formula (115) General formula (115) CN General formula (115) H 1016 General formula (115) General formula (115) CN H General formula (115) 1017 General formula (115) General formula (115) CN H H 1018 General formula (115) H CN General formula (115) H 1019 H General formula (115) CN General formula (115) H 1020 General formula (115) H CN H H 1021 General formula (115) General formula (115) CN General formula (115) F 1022 General formula (115) General formula (115) CN F General formula (115) 1023 General formula (115) General formula (115) CN F F 1024 General formula (115) F CN General formula (115) F 1025 F General formula (115) CN General formula (115) F 1026 General formula (115) F CN F F 1027 General formula (115) General formula (115) CN General formula (115) OH 1028 General formula (115) General formula (115) CN OH General formula (115) 1029 General formula (115) General formula (115) CN OH OH 1030 General formula (115) OH CN General formula (115) OH 1031 OH General formula (115) CN General formula (115) OH 1032 General formula (115) OH CN OH OH 1033 General formula (115) General formula (115) CN Cl General formula (115) 1034 General formula (115) General formula (115) CN Cl General formula (115) 1035 General formula (115) General formula (115) CN Cl General formula (115) 1036 General formula (115) General formula (115) CN Cl General formula (115) 1037 General formula (115) General formula (115) CN Cl General formula (115) 1038 General formula (115) General formula (115) CN Cl General formula (115) 1039 General formula (115) General formula (115) CN F General formula (115) 1040 General formula (115) General formula (115) CN F General formula (115) 1041 General formula (115) General formula (115) CN F General formula (115) 1042 General formula (115) General formula (115) CN F General formula (115) 1043 General formula (115) General formula (115) CN F General formula (115) 1044 General formula (115) General formula (115) CN F General formula (115) 1045 General formula (115) General formula (115) CN CH₃O General formula (115) 1046 General formula (115) General formula (115) CN CH₃O General formula (115) 1047 General formula (115) General formula (115) CN CH₃O General formula (115) 1048 General formula (115) General formula (115) CN CH₃O General formula (115) 1049 General formula (115) General formula (115) CN CH₃O General formula (115) 1050 General formula (115) General formula (115) CN CH₃O General formula (115) 1051 General formula (115) General formula (115) CN C₂H₅O General formula (115) 1052 General formula (115) General formula (115) CN C₂H₅O General formula (115) 1053 General formula (115) General formula (115) CN C₂H₅O General formula (115) 1054 General formula (115) General formula (115) CN C₂H₅O General formula (115) 1055 General formula (115) General formula (115) CN C₂H₅O General formula (115) 1056 General formula (115) General formula (115) CN C₂H₅O General formula (115) 1057 General formula (115) General formula (115) CN C₆H₅O General formula (115) 1058 General formula (115) General formula (115) CN C₆H₅O General formula (115) 1059 General formula (115) General formula (115) CN C₆H₅O General formula (115) 1060 General formula (115) General formula (115) CN C₆H₅O General formula (115) 1061 General formula (115) General formula (115) CN C₆H₅O General formula (115) 1062 General formula (115) General formula (115) CN C₆H₅O General formula (115) 1063 General formula (115) General formula (115) CN Formula (121) General formula (115) 1064 General formula (115) General formula (115) CN Formula (121) General formula (115) 1065 General formula (115) General formula (115) CN Formula (121) General formula (115) 1066 General formula (115) General formula (115) CN Formula (121) General formula (115) 1067 General formula (115) General formula (115) CN Formula (121) General formula (115) 1068 General formula (115) General formula (115) CN Formula (121) General formula (115) 1069 General formula (115) General formula (115) CN Formula (122) General formula (115) 1070 General formula (115) General formula (115) CN Formula (122) General formula (115) 1071 General formula (115) General formula (115) CN Formula (122) General formula (115) 1072 General formula (115) General formula (115) CN Formula (122) General formula (115) 1073 General formula (115) General formula (115) CN Formula (122) General formula (115) 1074 General formula (115) General formula (115) CN Formula (122) General formula (115) 1075 General formula (115) General formula (115) CN Formula (123) General formula (115) 1076 General formula (115) General formula (115) CN Formula (123) General formula (115) 1077 General formula (115) General formula (115) CN Formula (123) General formula (115) 1078 General formula (115) General formula (115) CN Formula (123) General formula (115) 1079 General formula (115) General formula (115) CN Formula (123) General formula (115) 1080 General formula (115) General formula (115) CN Formula (123) General formula (115) 1081 General formula (115) General formula (115) CN Formula (124) General formula (115) 1082 General formula (115) General formula (115) CN Formula (124) General formula (115) 1083 General formula (115) General formula (115) CN Formula (124) General formula (115) 1084 General formula (115) General formula (115) CN Formula (124) General formula (115) 1085 General formula (115) General formula (115) CN Formula (124) General formula (115) 1086 General formula (115) General formula (115) CN Formula (124) General formula (115) Compound General formula (115) No. R⁷¹, R⁸⁰ R⁷², R⁷⁹ R⁷³, R⁷⁸ R⁷⁴, R⁷⁷ R⁷⁵, R⁷⁶ 1001 H H H H H 1002 H CH₃ H H H 1003 H CH₃O H H H 1004 H C₆H₅ H H H 1005 H CH₃ H CH₃ H 1006 H CH₃O H CH₃O H 1007 H C₆H₅ H C₆H₅ H 1008 H H CH₃ H H 1009 H H CH₃O H H 1010 H H t-C₄H₉ H H 1011 H H Cl H H 1012 H H F H H 1013 H H C₆H₅ H H 1014 H H p-C₆H₅—C₆H₄ H H 1015 H H H H H 1016 H H H H H 1017 H H H H H 1018 H H H H H 1019 H H H H H 1020 H H H H H 1021 H H H H H 1022 H H H H H 1023 H H H H H 1024 H H H H H 1025 H H H H H 1026 H H H H H 1027 H H H H H 1028 H H H H H 1029 H H H H H 1030 H H H H H 1031 H H H H H 1032 H H H H H 1033 H H H H H 1034 H H CH₃ H H 1035 H H CH₃O H H 1036 H H t-C₄H₉ H H 1037 H H Cl H H 1038 H H F H H 1039 H H H H H 1040 H H CH₃ H H 1041 H H CH₃O H H 1042 H H t-C₄H₉ H H 1043 H H Cl H H 1044 H H F H H 1045 H H H H H 1046 H H CH₃ H H 1047 H H CH₃O H H 1048 H H t-C₄H₉ H H 1049 H H Cl H H 1050 H H F H H 1051 H H H H H 1052 H H CH₃ H H 1053 H H CH₃O H H 1054 H H t-C₄H₉ H H 1055 H H Cl H H 1056 H H F H H 1057 H H H H H 1058 H H CH₃ H H 1059 H H CH₃O H H 1060 H H t-C₄H₉ H H 1061 H H Cl H H 1062 H H F H H 1063 H H H H H 1064 H H CH₃ H H 1065 H H CH₃O H H 1066 H H t-C₄H₉ H H 1067 H H Cl H H 1068 H H F H H 1069 H H H H H 1070 H H CH₃ H H 1071 H H CH₃O H H 1072 H H t-C₄H₉ H H 1073 H H Cl H H 1074 H H F H H 1075 H H H H H 1076 H H CH₃ H H 1077 H H CH₃O H H 1078 H H t-C₄H₉ H H 1079 H H Cl H H 1080 H H F H H 1081 H H H H H 1082 H H CH₃ H H 1083 H H CH₃O H H 1084 H H t-C₄H₉ H H 1085 H H Cl H H 1086 H H F H H

Preferred delayed fluorescent materials include the following compounds.

[1] A compound represented by the following general formula (131):

[In the general formula (131), from 0 to 1 of R¹ to R⁵ represents a cyano group, from 1 to 5 of R¹ to R⁵ each represent a group represented by the following general formula (132), and the balance of R¹ to R⁵ each represent a hydrogen atom or a substituent other than the above.]

[In the general formula (132), R¹¹ to R²⁰ each independently represent a hydrogen atom or a substituent. R¹¹ and R¹², R¹² and R¹³, R¹³ and R¹⁴, R¹⁴ and R¹⁵, R¹⁵ and R¹⁶, R¹⁶ and R¹⁷, R¹⁷ and R¹⁸, R¹⁸ and R¹⁹, and R¹⁹ and R²⁰ each may be bonded to each other to form a cyclic structure. L¹² represents a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.] [2] The compound according to [1], wherein the group represented by the general formula (132) is a group represented by any one of the following general formulae (133) to (138):

[In the general formulae (133) to (138), R²¹ to R²⁴, R²⁷ to R³⁸, R⁴¹ to R⁴⁸, R⁵¹ to R⁵⁸, R⁶¹ to R⁶⁵, R⁷¹ to R⁷⁹, R⁸¹ to R⁹⁰ each independently represent a hydrogen atom or a substituent. R²¹ and R²², R²² and R²³, R²³ and R²⁴, R²⁷ and R²⁸, R⁸ and R⁹, R²⁹ and R³⁰, R³¹ and R³², R³² and R³³, R³³ and R³⁴, R³⁵ and R³⁶, R³⁶ and R³⁷, R³⁷ and R³⁸, R⁴¹ and R⁴², R⁴² and R⁴³, R⁴³ and R⁴⁴, R⁴⁵ and R⁴⁶, R⁴⁶ and R⁴⁷, R⁴⁷ and R⁴⁸, R⁵¹ and R⁵², R⁵² and R⁵³, R⁵³ and R⁵⁴, R⁵⁵ and R⁵⁶, R⁵⁶ and R⁵⁷, R⁵⁷ and R⁵⁸, R⁶¹ and R⁶², R⁶² and R⁶³, R⁶³ and R⁶⁴, R⁶⁴ and R⁶⁵, R⁵⁴ and R⁶¹, R⁵⁵ and R⁶⁵, R⁷¹ and R⁷², R⁷² and R⁷³, R⁷³ and R⁷⁴, R⁷⁴ and R⁷⁵, R⁷⁶ and R⁷⁷, R⁷⁷ and R⁷⁸, R⁷⁸ and R⁷⁹, R⁸¹ and R⁸², R⁸² and R⁸³, R⁸³ and R⁸⁴, R⁸⁵ and R⁸⁶, R⁸⁶ and R⁸⁷, R⁸⁷ and R⁸⁸, and R⁸⁹ and R⁹⁰ each may be bonded to each other to form a cyclic structure. L¹³ to L¹⁸ each independently represent a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.] [3] The compound according to [1] or [2], wherein in the general formula (131), R³ represents a cyano group. [4] The compound according to any one of [1] to [3], wherein in the general formula (131), R¹ and R⁴ each represent a group represented by the general formula (132). [5] The compound according to any one of [1] to [4], wherein in the general formula (132), L¹² represents a phenylene group. [6] The compound according to any one of [1] to [5], wherein the group represented by the general formula (132) is a group represented by the general formula (133). [7] The compound according to [6], wherein in the general formula (133), L¹³ represents a 1,3-phenylene group. [8] The compound according to any one of [1] to [5], wherein the group represented by the general formula (132) is a group represented by the general formula (134). [9] The compound according to [8], wherein in the general formula (134), L¹⁴ represents a 1,4-phenylene group. [10] The compound according to any one of [1] to [5], wherein the group represented by the general formula (132) is a group represented by the general formula (138). [11] The compound according to [10], wherein in the general formula (132), L¹⁸ represents a 1,4-phenylene group.

Examples of the compound include the following compounds.

Examples of the preferred delayed fluorescent material include compounds represented by the following general formula. The entire description of WO 2013/011954 including the paragraphs 0007 to 0047 and 0073 to 0085 is incorporated herein by reference as a part of the description of the present application.

[In the general formula (141), R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸ and R¹⁷ each independently represent a hydrogen atom or an electron donating group, provided that at least one thereof represents an electron donating group. R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ each independently represent a hydrogen atom or an electron withdrawing group having no unshared electron pair at the α-position. Z represents a single bond or >C═Y, wherein Y represents O, S, C(CN)₂ or C(COOH)₂, provided that when Z represents a single bond, at least one of R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ represents an electron withdrawing group having no unshared electron pair at the α-position.

Specific examples of the compounds include the compounds shown in the following Table 7 to Table 16. In the Tables, D1 to D3 represent the following aryl groups substituted by an electron donating group, respectively; A1 to A5 represent the following electron withdrawing groups, respectively; H represents a hydrogen atom; and Ph represents a phenyl group.

TABLE 7 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2001 H H A1 A1 Ph single bond H 2002 H D1 A1 A1 Ph single bond H 2003 H D2 A1 A1 Ph single bond H 2004 H D3 A1 A1 Ph single bond H 2005 H H A2 A2 Ph single bond H 2006 H D1 A2 A2 Ph single bond H 2007 H D2 A2 A2 Ph single bond H 2008 H D3 A2 A2 Ph single bond H 2009 H H A3 A3 Ph single bond H 2010 H D1 A3 A3 Ph single bond H 2011 H D2 A3 A3 Ph single bond H 2012 H D3 A3 A3 Ph single bond H 2013 H H A4 A4 Ph single bond H 2014 H D1 A4 A4 Ph single bond H 2015 H D2 A4 A4 Ph single bond H 2016 H D3 A4 A4 Ph single bond H 2017 H H A5 A5 Ph single bond H 2018 H D1 A5 A5 Ph single bond H 2019 H D2 A5 A5 Ph single bond H 2020 H D3 A5 A5 Ph single bond H 2021 D1 D1 A1 A1 Ph single bond H 2022 D2 D2 A1 A1 Ph single bond H 2023 D3 D3 A1 A1 Ph single bond H 2024 D1 D1 A2 A2 Ph single bond H 2025 D2 D2 A2 A2 Ph single bond H 2026 D3 D3 A2 A2 Ph single bond H 2027 D1 D1 A3 A3 Ph single bond H 2028 D2 D2 A3 A3 Ph single bond H 2029 D3 D3 A3 A3 Ph single bond H 2030 D1 D1 A4 A4 Ph single bond H 2031 D2 D2 A4 A4 Ph single bond H 2032 D3 D3 A4 A4 Ph single bond H 2033 D1 D1 A5 A5 Ph single bond H 2034 D2 D2 A5 A5 Ph single bond H 2035 D3 D3 A5 A5 Ph single bond H

TABLE 8 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2036 H H H A1 Ph single bond H 2037 H D1 H A1 Ph single bond H 2038 H D2 H A1 Ph single bond H 2039 H D3 H A1 Ph single bond H 2040 H H H A2 Ph single bond H 2041 H D1 H A2 Ph single bond H 2042 H D2 H A2 Ph single bond H 2043 H D3 H A2 Ph single bond H 2044 H H H A3 Ph single bond H 2045 H D1 H A3 Ph single bond H 2046 H D2 H A3 Ph single bond H 2047 H D3 H A3 Ph single bond H 2048 H H H A4 Ph single bond H 2049 H D1 H A4 Ph single bond H 2050 H D2 H A4 Ph single bond H 2051 H D3 H A4 Ph single bond H 2052 H H H A5 Ph single bond H 2053 H D1 H A5 Ph single bond H 2054 H D2 H A5 Ph single bond H 2055 H D3 H A5 Ph single bond H 2056 D1 D1 H A1 Ph single bond H 2057 D2 D2 H A1 Ph single bond H 2058 D3 D3 H A1 Ph single bond H 2059 D1 D1 H A2 Ph single bond H 2060 D2 D2 H A2 Ph single bond H 2061 D3 D3 H A2 Ph single bond H 2062 D1 D1 H A3 Ph single bond H 2063 D2 D2 H A3 Ph single bond H 2064 D3 D3 H A3 Ph single bond H 2065 D1 D1 H A4 Ph single bond H 2066 D2 D2 H A4 Ph single bond H 2067 D3 D3 H A4 Ph single bond H 2068 D1 D1 H A5 Ph single bond H 2069 D2 D2 H A5 Ph single bond H 2070 D3 D3 H A5 Ph single bond H

TABLE 9 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2071 H H A1 A1 Ph C═O H 2072 H D1 A1 A1 Ph C═O H 2073 H D2 A1 A1 Ph C═O H 2074 H D3 A1 A1 Ph C═O H 2075 H H A2 A2 Ph C═O H 2076 H D1 A2 A2 Ph C═O H 2077 H D2 A2 A2 Ph C═O H 2078 H D3 A2 A2 Ph C═O H 2079 H H A3 A3 Ph C═O H 2080 H D1 A3 A3 Ph C═O H 2081 H D2 A3 A3 Ph C═O H 2082 H D3 A3 A3 Ph C═O H 2083 H H A4 A4 Ph C═O H 2084 H D1 A4 A4 Ph C═O H 2085 H D2 A4 A4 Ph C═O H 2086 H D3 A4 A4 Ph C═O H 2087 H H A5 A5 Ph C═O H 2088 H D1 A5 A5 Ph C═O H 2089 H D2 A5 A5 Ph C═O H 2090 H D3 A5 A5 Ph C═O H 2091 D1 D1 A1 A1 Ph C═O H 2092 D2 D2 A1 A1 Ph C═O H 2093 D3 D3 A1 A1 Ph C═O H 2094 D1 D1 A2 A2 Ph C═O H 2095 D2 D2 A2 A2 Ph C═O H 2096 D3 D3 A2 A2 Ph C═O H 2097 D1 D1 A3 A3 Ph C═O H 2098 D2 D2 A3 A3 Ph C═O H 2099 D3 D3 A3 A3 Ph C═O H 2100 D1 D1 A4 A4 Ph C═O H 2101 D2 D2 A4 A4 Ph C═O H 2102 D3 D3 A4 A4 Ph C═O H 2103 D1 D1 A5 A5 Ph C═O H 2104 D2 D2 A5 A5 Ph C═O H 2105 D3 D3 A5 A5 Ph C═O H

TABLE 10 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2106 H H H A1 Ph C═O H 2107 H D1 H A1 Ph C═O H 2108 H D2 H A1 Ph C═O H 2109 H D3 H A1 Ph C═O H 2110 H H H A2 Ph C═O H 2111 H D1 H A2 Ph C═O H 2112 H D2 H A2 Ph C═O H 2113 H D3 H A2 Ph C═O H 2114 H H H A3 Ph C═O H 2115 H D1 H A3 Ph C═O H 2116 H D2 H A3 Ph C═O H 2117 H D3 H A3 Ph C═O H 2118 H H H A4 Ph C═O H 2119 H D1 H A4 Ph C═O H 2120 H D2 H A4 Ph C═O H 2121 H D3 H A4 Ph C═O H 2122 H H H A5 Ph C═O H 2123 H D1 H A5 Ph C═O H 2124 H D2 H A5 Ph C═O H 2125 H D3 H A5 Ph C═O H 2126 D1 D1 H A1 Ph C═O H 2127 D2 D2 H A1 Ph C═O H 2128 D3 D3 H A1 Ph C═O H 2129 D1 D1 H A2 Ph C═O H 2130 D2 D2 H A2 Ph C═O H 2131 D3 D3 H A2 Ph C═O H 2132 D1 D1 H A3 Ph C═O H 2133 D2 D2 H A3 Ph C═O H 2134 D3 D3 H A3 Ph C═O H 2135 D1 D1 H A4 Ph C═O H 2136 D2 D2 H A4 Ph C═O H 2137 D3 D3 H A4 Ph C═O H 2138 D1 D1 H A5 Ph C═O H 2139 D2 D2 H A5 Ph C═O H 2140 D3 D3 H A5 Ph C═O H 2141 H H H H Ph C═O H

TABLE 11 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2142 H H A1 A1 Ph C═S H 2143 H D1 A1 A1 Ph C═S H 2144 H D2 A1 A1 Ph C═S H 2145 H D3 A1 A1 Ph C═S H 2146 H H A2 A2 Ph C═S H 2147 H D1 A2 A2 Ph C═S H 2148 H D2 A2 A2 Ph C═S H 2149 H D3 A2 A2 Ph C═S H 2150 H H A3 A3 Ph C═S H 2151 H D1 A3 A3 Ph C═S H 2152 H D2 A3 A3 Ph C═S H 2153 H D3 A3 A3 Ph C═S H 2154 H H A4 A4 Ph C═S H 2155 H D1 A4 A4 Ph C═S H 2156 H D2 A4 A4 Ph C═S H 2157 H D3 A4 A4 Ph C═S H 2158 H H A5 A5 Ph C═S H 2159 H D1 A5 A5 Ph C═S H 2160 H D2 A5 A5 Ph C═S H 2161 H D3 A5 A5 Ph C═S H 2162 D1 D1 A1 A1 Ph C═S H 2163 D2 D2 A1 A1 Ph C═S H 2164 D3 D3 A1 A1 Ph C═S H 2165 D1 D1 A2 A2 Ph C═S H 2166 D2 D2 A2 A2 Ph C═S H 2167 D3 D3 A2 A2 Ph C═S H 2168 D1 D1 A3 A3 Ph C═S H 2169 D2 D2 A3 A3 Ph C═S H 2170 D3 D3 A3 A3 Ph C═S H 2171 D1 D1 A4 A4 Ph C═S H 2172 D2 D2 A4 A4 Ph C═S H 2173 D3 D3 A4 A4 Ph C═S H 2174 D1 D1 A5 A5 Ph C═S H 2175 D2 D2 A5 A5 Ph C═S H 2176 D3 D3 A5 A5 Ph C═S H

TABLE 12 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2177 H H H A1 Ph C═S H 2178 H D1 H A1 Ph C═S H 2179 H D2 H A1 Ph C═S H 2180 H D3 H A1 Ph C═S H 2181 H H H A2 Ph C═S H 2182 H D1 H A2 Ph C═S H 2183 H D2 H A2 Ph C═S H 2184 H D3 H A2 Ph C═S H 2185 H H H A3 Ph C═S H 2186 H D1 H A3 Ph C═S H 2187 H D2 H A3 Ph C═S H 2188 H D3 H A3 Ph C═S H 2189 H H H A4 Ph C═S H 2190 H D1 H A4 Ph C═S H 2191 H D2 H A4 Ph C═S H 2192 H D3 H A4 Ph C═S H 2193 H H H A5 Ph C═S H 2194 H D1 H A5 Ph C═S H 2195 H D2 H A5 Ph C═S H 2196 H D3 H A5 Ph C═S H 2197 D1 D1 H A1 Ph C═S H 2198 D2 D2 H A1 Ph C═S H 2199 D3 D3 H A1 Ph C═S H 2200 D1 D1 H A2 Ph C═S H 2201 D2 D2 H A2 Ph C═S H 2202 D3 D3 H A2 Ph C═S H 2203 D1 D1 H A3 Ph C═S H 2204 D2 D2 H A3 Ph C═S H 2205 D3 D3 H A3 Ph C═S H 2206 D1 D1 H A4 Ph C═S H 2207 D2 D2 H A4 Ph C═S H 2208 D3 D3 H A4 Ph C═S H 2209 D1 D1 H A5 Ph C═S H 2210 D2 D2 H A5 Ph C═S H 2211 D3 D3 H A5 Ph C═S H 2212 H H H H Ph C═S H

TABLE 13 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2213 H H A1 A1 Ph C═C(CN)₂ H 2214 H D1 A1 A1 Ph C═C(CN)₂ H 2215 H D2 A1 A1 Ph C═C(CN)₂ H 2216 H D3 A1 A1 Ph C═C(CN)₂ H 2217 H H A2 A2 Ph C═C(CN)₂ H 2218 H D1 A2 A2 Ph C═C(CN)₂ H 2219 H D2 A2 A2 Ph C═C(CN)₂ H 2220 H D3 A2 A2 Ph C═C(CN)₂ H 2221 H H A3 A3 Ph C═C(CN)₂ H 2222 H D1 A3 A3 Ph C═C(CN)₂ H 2223 H D2 A3 A3 Ph C═C(CN)₂ H 2224 H D3 A3 A3 Ph C═C(CN)₂ H 2225 H H A4 A4 Ph C═C(CN)₂ H 2226 H D1 A4 A4 Ph C═C(CN)₂ H 2227 H D2 A4 A4 Ph C═C(CN)₂ H 2228 H D3 A4 A4 Ph C═C(CN)₂ H 2229 H H A5 A5 Ph C═C(CN)₂ H 2230 H D1 A5 A5 Ph C═C(CN)₂ H 2231 H D2 A5 A5 Ph C═C(CN)₂ H 2232 H D3 A5 A5 Ph C═C(CN)₂ H 2233 D1 D1 A1 A1 Ph C═C(CN)₂ H 2234 D2 D2 A1 A1 Ph C═C(CN)₂ H 2235 D3 D3 A1 A1 Ph C═C(CN)₂ H 2236 D1 D1 A2 A2 Ph C═C(CN)₂ H 2237 D2 D2 A2 A2 Ph C═C(CN)₂ H 2238 D3 D3 A2 A2 Ph C═C(CN)₂ H 2239 D1 D1 A3 A3 Ph C═C(CN)₂ H 2240 D2 D2 A3 A3 Ph C═C(CN)₂ H 2241 D3 D3 A3 A3 Ph C═C(CN)₂ H 2242 D1 D1 A4 A4 Ph C═C(CN)₂ H 2243 D2 D2 A4 A4 Ph C═C(CN)₂ H 2244 D3 D3 A4 A4 Ph C═C(CN)₂ H 2245 D1 D1 A5 A5 Ph C═C(CN)₂ H 2246 D2 D2 A5 A5 Ph C═C(CN)₂ H 2247 D3 D3 A5 A5 Ph C═C(CN)₂ H

TABLE 14 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2248 H H H A1 Ph C═C(CN)₂ H 2249 H D1 H A1 Ph C═C(CN)₂ H 2250 H D2 H A1 Ph C═C(CN)₂ H 2251 H D3 H A1 Ph C═C(CN)₂ H 2252 H H H A2 Ph C═C(CN)₂ H 2253 H D1 H A2 Ph C═C(CN)₂ H 2254 H D2 H A2 Ph C═C(CN)₂ H 2255 H D3 H A2 Ph C═C(CN)₂ H 2256 H H H A3 Ph C═C(CN)₂ H 2257 H D1 H A3 Ph C═C(CN)₂ H 2258 H D2 H A3 Ph C═C(CN)₂ H 2259 H D3 H A3 Ph C═C(CN)₂ H 2260 H H H A4 Ph C═C(CN)₂ H 2261 H D1 H A4 Ph C═C(CN)₂ H 2262 H D2 H A4 Ph C═C(CN)₂ H 2263 H D3 H A4 Ph C═C(CN)₂ H 2264 H H H A5 Ph C═C(CN)₂ H 2265 H D1 H A5 Ph C═C(CN)₂ H 2266 H D2 H A5 Ph C═C(CN)₂ H 2267 H D3 H A5 Ph C═C(CN)₂ H 2268 D1 D1 H A1 Ph C═C(CN)₂ H 2269 D2 D2 H A1 Ph C═C(CN)₂ H 2270 D3 D3 H A1 Ph C═C(CN)₂ H 2271 D1 D1 H A2 Ph C═C(CN)₂ H 2272 D2 D2 H A2 Ph C═C(CN)₂ H 2273 D3 D3 H A2 Ph C═C(CN)₂ H 2274 D1 D1 H A3 Ph C═C(CN)₂ H 2275 D2 D2 H A3 Ph C═C(CN)₂ H 2276 D3 D3 H A3 Ph C═C(CN)₂ H 2277 D1 D1 H A4 Ph C═C(CN)₂ H 2278 D2 D2 H A4 Ph C═C(CN)₂ H 2279 D3 D3 H A4 Ph C═C(CN)₂ H 2280 D1 D1 H A5 Ph C═C(CN)₂ H 2281 D2 D2 H A5 Ph C═C(CN)₂ H 2282 D3 D3 H A5 Ph C═C(CN)₂ H 2283 H H H H Ph C═C(CN)₂ H

TABLE 15 Compound No. R² R⁷ R¹⁰ R¹⁵ R¹⁷ Z Other Rs 2284 H H A1 A1 Ph C═C(COOH)₂ H 2285 H D1 A1 A1 Ph C═C(COOH)₂ H 2286 H D2 A1 A1 Ph C═C(COOH)₂ H 2287 H D3 A1 A1 Ph C═C(COOH)₂ H 2288 H H A2 A2 Ph C═C(COOH)₂ H 2289 H D1 A2 A2 Ph C═C(COOH)₂ H 2290 H D2 A2 A2 Ph C═C(COOH)₂ H 2291 H D3 A2 A2 Ph C═C(COOH)₂ H 2292 H H A3 A3 Ph C═C(COOH)₂ H 2293 H D1 A3 A3 Ph C═C(COOH)₂ H 2294 H D2 A3 A3 Ph C═C(COOH)₂ H 2295 H D3 A3 A3 Ph C═C(COOH)₂ H 2296 H H A4 A4 Ph C═C(COOH)₂ H 2297 H D1 A4 A4 Ph C═C(COOH)₂ H 2298 H D2 A4 A4 Ph C═C(COOH)₂ H 2299 H D3 A4 A4 Ph C═C(COOH)₂ H 2300 H H A5 A5 Ph C═C(COOH)₂ H 2301 H D1 A5 A5 Ph C═C(COOH)₂ H 2302 H D2 A5 A5 Ph C═C(COOH)₂ H 2303 H D3 A5 A5 Ph C═C(COOH)₂ H 2304 D1 D1 A1 A1 Ph C═C(COOH)₂ H 2305 D2 D2 A1 A1 Ph C═C(COOH)₂ H 2306 D3 D3 A1 A1 Ph C═C(COOH)₂ H 2307 D1 D1 A2 A2 Ph C═C(COOH)₂ H 2308 D2 D2 A2 A2 Ph C═C(COOH)₂ H 2309 D3 D3 A2 A2 Ph C═C(COOH)₂ H 2310 D1 D1 A3 A3 Ph C═C(COOH)₂ H 2311 D2 D2 A3 A3 Ph C═C(COOH)₂ H 2312 D3 D3 A3 A3 Ph C═C(COOH)₂ H 2313 D1 D1 A4 A4 Ph C═C(COOH)₂ H 2314 D2 D2 A4 A4 Ph C═C(COOH)₂ H 2315 D3 D3 A4 A4 Ph C═C(COOH)₂ H 2316 D1 D1 A5 A5 Ph C═C(COOH)₂ H 2317 D2 D2 A5 A5 Ph C═C(COOH)₂ H 2318 D3 D3 A5 A5 Ph C═C(COOH)₂ H

TABLE 16 Compound No. R³ R⁶ R¹¹ R¹⁴ R¹⁷ Z Other Rs 2319 H H H A1 Ph C═C(COOH)₂ H 2320 H D1 H A1 Ph C═C(COOH)₂ H 2321 H D2 H A1 Ph C═C(COOH)₂ H 2322 H D3 H A1 Ph C═C(COOH)₂ H 2323 H H H A2 Ph C═C(COOH)₂ H 2324 H D1 H A2 Ph C═C(COOH)₂ H 2325 H D2 H A2 Ph C═C(COOH)₂ H 2326 H D3 H A2 Ph C═C(COOH)₂ H 2327 H H H A3 Ph C═C(COOH)₂ H 2328 H D1 H A3 Ph C═C(COOH)₂ H 2329 H D2 H A3 Ph C═C(COOH)₂ H 2330 H D3 H A3 Ph C═C(COOH)₂ H 2331 H H H A4 Ph C═C(COOH)₂ H 2332 H D1 H A4 Ph C═C(COOH)₂ H 2333 H D2 H A4 Ph C═C(COOH)₂ H 2334 H D3 H A4 Ph C═C(COOH)₂ H 2335 H H H A5 Ph C═C(COOH)₂ H 2336 H D1 H A5 Ph C═C(COOH)₂ H 2337 H D2 H A5 Ph C═C(COOH)₂ H 2338 H D3 H A5 Ph C═C(COOH)₂ H 2339 D1 D1 H A1 Ph C═C(COOH)₂ H 2340 D2 D2 H A1 Ph C═C(COOH)₂ H 2341 D3 D3 H A1 Ph C═C(COOH)₂ H 2342 D1 D1 H A2 Ph C═C(COOH)₂ H 2343 D2 D2 H A2 Ph C═C(COOH)₂ H 2344 D3 D3 H A2 Ph C═C(COOH)₂ H 2345 D1 D1 H A3 Ph C═C(COOH)₂ H 2346 D2 D2 H A3 Ph C═C(COOH)₂ H 2347 D3 D3 H A3 Ph C═C(COOH)₂ H 2348 D1 D1 H A4 Ph C═C(COOH)₂ H 2349 D2 D2 H A4 Ph C═C(COOH)₂ H 2350 D3 D3 H A4 Ph C═C(COOH)₂ H 2351 D1 D1 H A5 Ph C═C(COOH)₂ H 2352 D2 D2 H A5 Ph C═C(COOH)₂ H 2353 D3 D3 H A5 Ph C═C(COOH)₂ H 2354 H H H H Ph C═C(COOH)₂ H

Examples of the preferred delayed fluorescent material include compounds represented by the following general formula. The entire description of WO 2013/011955 including the paragraphs 0007 to 0033 and 0059 to 0066 is incorporated herein by reference as a part of the description of the present application.

[In the general formula (151), R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ each independently represent a hydrogen atom or an electron donating group, provided that at least one thereof represents an electron donating group. R⁹, R¹⁰, R¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ each independently represent a hydrogen atom or an electron withdrawing group, provided that at least one thereof represents an electron withdrawing group.]

Specific examples of the compounds include the compounds shown in the following Table 17 to Table 20. In the Tables, D11 to D20 represent the unsubstituted electron donating groups having the following structures, respectively.

TABLE 17 Compound No. R² R⁷ R¹⁰ R¹⁵ Other Rs 3002 D11 D11 CN CN H 3003 D12 D12 CN CN H 3004 D13 D13 CN CN H 3005 D14 D14 CN CN H 3006 D15 D15 CN CN H 3007 D16 D16 CN CN H 3008 D17 D17 CN CN H 3009 D18 D18 CN CN H 3010 D19 D19 CN CN H 3011 D20 D20 CN CN H 3012 H D11 H CN H 3013 H D12 H CN H 3014 H D13 H CN H 3015 H D14 H CN H 3016 H D15 H CN H 3017 H D16 H CN H 3018 H D17 H CN H 3019 H D18 H CN H 3020 H D19 H CN H 3021 H D20 H CN H

TABLE 18 Compound No. R³ R⁶ R¹¹ R¹⁴ Other Rs 3022 D11 D11 CN CN H 3023 D12 D12 CN CN H 3024 D13 D13 CN CN H 3025 D14 D14 CN CN H 3026 D15 D15 CN CN H 3027 D16 D16 CN CN H 3028 D17 D17 CN CN H 3029 D18 D18 CN CN H 3030 D19 D19 CN CN H 3031 D20 D20 CN CN H 3032 H D11 H CN H 3033 H D12 H CN H 3034 H D13 H CN H 3035 H D14 H CN H 3036 H D15 H CN H 3037 H D16 H CN H 3038 H D17 H CN H 3039 H D18 H CN H 3040 H D19 H CN H 3041 H D20 H CN H

TABLE 19 Compound No. R², R⁷ R³, R⁶ R¹⁰, R¹⁵ R¹¹, R¹⁴ Other Rs 3042 diphenylamino group H CN H H 3043 bis(2-methylphenyl)amino group H CN H H 3044 bis(3-methylphenyl)amino group H CN H H 3045 bis(2,4-dimethylphenyl)amino group H CN H H 3046 bis(2,6-dimethylphenyl)amino group H CN H H 3047 bis(3,5-dimethylphenyl)amino group H CN H H 3048 bis(2,4,6-trimethylphenyl)amino group H CN H H 3049 bis(4-ethylphenyl)amino group H CN H H 3050 bis(4-propylphenyl)amino group H CN H H 3051 diphenylamino group H H CN H 3052 bis(2-methylphenyl)amino group H H CN H 3053 bis(3-methylphenyl)amino group H H CN H 3054 bis(4-methylphenyl)amino group H H CN H 3055 bis(2,4-dimethylphenyl)amino group H H CN H 3056 bis(2,6-dimethylphenyl)amino group H H CN H 3057 bis(3,5-dimethylphenyl)amino group H H CN H 3058 bis(2,4,6-trimethylphenyl)amino group H H CN H 3059 bis(4-ethylphenyl)amino group H H CN H 3060 bis(4-propylphenyl)amino group H H CN H

TABLE 20 Compound No. R², R⁷ R³, R⁶ R¹⁰, R¹⁵ R¹¹, R¹⁴ Other Rs 3061 H diphenylamino group CN H H 3062 H bis(2-methylphenyl)amino group CN H H 3063 H bis(3-methylphenyl)amino group CN H H 3064 H bis(4-methylphenyl)amino group CN H H 3065 H bis(2,4-dimethylphenyl)amino group CN H H 3066 H bis(2,6-dimethylphenyl)amino group CN H H 3067 H bis(3,5-dimethylphenyl)amino group CN H H 3068 H bis(2,4,6-trimethylphenyl)amino group CN H H 3069 H bis(4-ethylphenyl)amino group CN H H 3070 H bis(4-propylphenyl)amino group CN H H 3071 H diphenylamino group H CN H 3072 H bis(2-methylphenyl)amino group H CN H 3073 H bis(3-methylphenyl)amino group H CN H 3074 H bis(4-methylphenyl)amino group H CN H 3075 H bis(2,4-dimethylphenyl)amino group H CN H 3076 H bis(2,6-dimethylphenyl)amino group H CN H 3077 H bis(3,5-dimethylphenyl)amino group H CN H 3078 H bis(2,4,6-trimethylphenyl)amino group H CN H 3079 H bis(4-ethylphenyl)amino group H CN H 3080 H bis(4-propylphenyl)amino group H CN H

Examples of the preferred delayed fluorescent material include compounds represented by the following general formula. The entire description of WO 2013/081088 including the paragraphs 0008 to 0071 and 0118 to 0133 is incorporated herein by reference as a part of the description of the present application.

[In the general formula (161), any two of Y¹, Y² and Y³ each represent a nitrogen atom, and the balance thereof represents a methine group, of all Y¹, Y² and Y³ each represent a nitrogen atom. Z¹ and Z² each independently represent a hydrogen atom or a substituent. R¹ to R⁸ each independently represent a hydrogen atom or a substituent, provided that at least one of R¹ to R⁸ represents a substituted or unsubstituted diarylamino group or a substituted or unsubstituted carbazolyl group. The compound represented by the general formula (161) has at least two carbazole structures in the molecule thereof.

Examples of the compound include the following compounds.

Examples of the preferred delayed fluorescent material include compounds represented by the following general formula. The entire description of JP-A-2013-256490 including the paragraphs 0009 to 0046 and 0093 to 0134 is incorporated herein by reference as a part of the description of the present application.

[In the general formula (171), Ar¹ to Ar³ each independently represent a substituted or unsubstituted aryl group, and at least one of them represents a substituted aryl group represented by the following general formula (172).]

[In the general formula (172), R¹ to R⁸ each independently represent a hydrogen atom or a substituent. Z represents O, S, O═C or Ar⁴—N, Ar⁴ represents a substituted or unsubstituted aryl group. R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, and R⁷ and R⁸ each independently may be bonded to each other to form a cyclic structure.]

Examples of the compound include the following compounds.

Examples of the preferred delayed fluorescent material include compounds represented by the following general formula. The entire description of JP-A-2013-116975 including the paragraphs 0008 to 0020 and 0038 to 0040 is incorporated herein by reference as a part of the description of the present application.

[In the general formula (R¹, R², R⁴ to R⁸, R¹¹, R¹² and R¹⁴ to R¹⁸ each independently represent a hydrogen atom or a substituent.]

Examples of the preferred delayed fluorescent material include the following compounds.

[1] A compound represented by the following general formula (191):

[In the general formula (191), Ar¹ represents a substituted or unsubstituted arylene group; Ar² and Ar³ each independently represent a substituted or unsubstituted aryl group. R¹ to R⁸ each independently represent a hydrogen atom or a substituent, provided that at least one of R¹ to R⁸ represents a substituted or unsubstituted diarylamino group, and R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, and R⁷ and R⁸ each may be bonded to each other to form a cyclic structure. [2] The compound according to [1], wherein in the general formula (191), at least one of R¹ to R⁴ represents a substituted or unsubstituted diarylamino group, and at least one of R⁵ to R⁸ represents a substituted or unsubstituted diarylamino group. [3] The compound according to [2], wherein in the general formula (191), R³ and R⁶ each represent a substituted or unsubstituted diarylamino group. [4] The compound according to any one of [1] to [3], wherein in the general formula (191), at least one of R¹ to R⁸ represents a substituted or unsubstituted diphenylamino group. [5] The compound according to any one of [1] to [4], wherein in the general formula (191), Ar² and Ar³ each independently represent a substituted or unsubstituted phenyl group. [6] The compound according to any one of [1] to [5], wherein in the general formula (191), Ar¹ each independently represents a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group or a substituted or unsubstituted anthracenylene group. [7] The compound according to [1], wherein the compound has a structure represented by the following general formula (192):

[In the general formula (192), R¹ to R⁸ and R¹¹ to R²⁴ each independently represent a hydrogen atom or a substituent, provided that at least one of R¹ to R⁸ represents a substituted or unsubstituted diarylamino group, and R¹ and R², R² and R³, R³ and R⁴, R⁵ and R⁶, R⁶ and R⁷, R⁷ and R⁸, R¹¹ and R¹²; R¹² and R¹³, R¹³ and R¹⁴, R¹⁴ and R¹⁵, R¹⁶ and R¹⁷, R¹⁷ and R¹⁸, R¹⁸ and R¹⁹, R¹⁹ and R²⁰, R²¹ and R²², and R²³ and R²⁴ each may be bonded to each other to form a cyclic structure.] [8] The compound according to [7], wherein in the general formula (192), at least one of R¹ to R⁴ represents a substituted or unsubstituted diarylamino group, and at least one of R⁵ to R⁸ represents a substituted or unsubstituted diarylamino group. [9] The compound according to [8], wherein in the general formula (192), R³ and R⁶ each represent a substituted or unsubstituted diarylamino group.

Specific examples of the compound include the following compounds. Ph represents a phenyl group.

Examples of the preferred delayed fluorescent material include the following compounds.

[1] A compound represented by the following general formula (201):

(In the above formula, R¹ to R⁸ each independently represent a hydrogen atom or a substituent, provided that at least one of R¹ to R⁸ represents a substituted or unsubstituted carbazolyl group. Ar¹ to Ar³ each independently represent a substituted or unsubstituted aromatic ring or a heteroaromatic ring) [2] The compound according to [1], wherein in the general formula (201), at least one of R³ and R⁶ represents a substituted or unsubstituted carbazolyl group. [3] The compound according to [1] or [2], wherein the carbazolyl group is a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group or a 4-carbazolyl group. [4] The compound according to any one of [1] to [3], wherein the carbazolyl group has a substituent on the nitrogen atom in the carbazole cyclic structure. [5] The compound according to any one of [1] to [4], wherein in the general formula (201), at least one of Ar¹, Ar² and Ar³ represents a benzene ring or a naphthalene ring. [6] The compound according to any one of [1] to [5], wherein in the general formula (201), Ar¹, Ar² and Ar³ each represent the same aromatic ring or the same heteroaromatic ring. [7] The compound according to any one of [1] to [6], wherein in the general formula (201), Ar¹, Ar² and Ar³ each represent a benzene ring.

Examples of the compound include the following compounds.

Examples of the preferred delayed fluorescent material include compounds represented by the following general formulae. The entire description of WO 2013/133359 including the paragraphs 0007 to 0032 and 0079 to 0084 is incorporated herein by reference as a part of the description of the present application.

[In the general formula (212), Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ each independently represent a substituted or unsubstituted aryl group.]

Specific examples of the compound represented by the general formula (212) include the compound represented by the following structural formula.

Specific examples of the compound represented by the general formula (212) include the compounds shown in the following table. Here, Ar¹, Ar², Ar³, Ar⁴, Ar⁵ and Ar⁶ are the same as each other, and are expressed by Ar.

TABLE 21 Compound No. Ar 4002 4-fluorophenyl 4003 3-fluorophenyl 4004 2-fluorophenyl 4005 3,5-difluorophenyl 4006 2,4,6-trifluorophenyl 4007 4-methylphenyl 4008 3-methylphenyl 4009 2-methylphenyl 4010 3,5-dimethylphenyl 4011 2,4,6-trimethylphenyl 4012 4-ethylphenyl 4013 3-ethylphenyl 4014 2-ethylphenyl 4015 3,5-diethylphenyl 4016 4-propylphenyl 4017 3-propylphenyl 4018 3,5-dipropylphenyl 4019 4-tert-butylphenyl 4020 3-tert-butylphenyl 4021 3,5-di-tert-butylphenyl 4022 1-naphthyl 4023 2-naphthyl

Examples of the preferred delayed fluorescent material include compounds represented by the following general formula. The entire description of WO 2013/161437 including the paragraphs 0008 to 0054 and 0101 to 0121 is incorporated herein by reference as a part of the description of the present application.

[In the general formula (221), R¹ to R¹⁰ each independently represent a hydrogen atom or a substituent, provided that at least one of R¹ to R¹⁰ represents a substituted or unsubstituted aryl group, a substituted or unsubstituted diarylamino group or a substituted or unsubstituted 9-carbazolyl group. R¹ and R², R² and R³, R³ and R⁴, R⁴ and R⁵, R⁵ and R⁶, R⁶ and R⁷, R⁷ and R⁸, R⁸ and R⁹, and R⁹ and R¹⁰ each may be bonded to each other to form a cyclic structure.]

Specific examples of the compound include the following compounds.

Examples of the preferred delayed fluorescent material include compounds represented by the following general formula. The entire description of JP-A-2014-9352 including the paragraphs 0007 to 0041 and 0060 to 0069 is incorporated herein by reference as a part of the description of the present application.

[In the general formula (231), R¹ to R⁴ each independently represent a hydrogen atom or a substituted or unsubstituted (N,N-diarylamino)aryl group, provided that at least one of R¹ to R⁴ represents a substituted or unsubstituted (N,N-diarylamino)aryl group. Two aryl groups constituting the diarylamino moiety of the (N,N-diarylamino)aryl group may be bonded to each other. W¹, W², X¹, X², Y¹, Y², Z¹ and Z² each independently represent a carbon atom or a nitrogen atom. m¹ to m⁴ each independently represent 0, 1 or 2.]

Examples of the compound include the following compounds.

Examples of the preferred delayed fluorescent material include compounds represented by the following general formula. The entire description of JP-A-2014-9224 including the paragraphs 0008 to 0048 and 0067 to 0076 is incorporated herein by reference as a part of the description of the present application.

[In the general formula (241), R¹ to R⁶ each independently represent a hydrogen atom or a substituent, provided that at least one of R¹ to R⁶ represents a substituted or unsubstituted (N,N-diarylamino)aryl group, and two aryl groups constituting the diarylamino moiety of the (N,N-diarylamino)aryl group may be bonded to each other. X¹ to X and Y¹ to Y⁶ each independently represent a carbon atom or a nitrogen atom. n¹, n², p¹, p², q¹ and q² each independently represent 0, 1 or 2.]

Examples of the compound include the following compounds.

Preferred compounds for host materials that can be used together with the host material for delayed fluorescent materials of the present invention are mentioned below.

Preferred examples of compounds usable as a hole injection material are mentioned below.

Next, preferred examples of compounds usable as a hole transport material are mentioned below.

Next, preferred examples of compounds usable as a hole barrier material are mentioned below.

Next, preferred examples of compounds usable as a hole barrier material are mentioned below.

Next, preferred examples of compounds usable as a hole transport material are mentioned below.

Next, preferred examples of compounds usable as an electron injection material are mentioned below.

Further, preferred examples of additive compounds are mentioned below. For example, the compounds may be added as a stabilization material.

The organic electroluminescence device thus produced by the aforementioned method emits light on application of an electric field between the anode and the cathode of the device. In this case, when the light emission is caused by the excited singlet energy, light having a wavelength that corresponds to the energy level thereof may be confirmed as fluorescent light and delayed fluorescent light. When the light emission is caused by the excited triplet energy, light having a wavelength that corresponds to the energy level thereof may be confirmed as phosphorescent light. The normal fluorescent light has a shorter light emission lifetime than the delayed fluorescent light, and thus the light emission lifetime may be distinguished between the fluorescent light and the delayed fluorescent light.

On the other hand, the phosphorescent light could not be substantially observed with a normal organic compound, such as the compound of the invention, at room temperature since the excited triplet energy is converted to heat or the like due to the instability thereof, and is immediately deactivated with a short lifetime. The excited triplet energy of the normal organic compound may be measured by observing light emission under an extremely low temperature condition.

The organic electroluminescence device of the invention may be applied to any of a single device, a structure with plural devices disposed in an array, and a structure having anodes and cathodes disposed in an X-Y matrix. According to the invention, an organic light-emitting device that is largely improved in light emission efficiency may be obtained by adding the compound represented by the general formula (1) to the light-emitting layer. The organic light-emitting device, such as the organic electroluminescence device, of the invention may be applied to a further wide range of purposes. For example, an organic electroluminescent display apparatus may be produced with the organic electroluminescence device of the invention, and for the details thereof, reference may be made to Seiji Tokito, Chihaya Adachi and Hideyuki Murata, “Yuki EL Display” (Organic EL Display) (Ohm-sha, Ltd.). In particular, the organic electroluminescence device of the invention may be applied to organic electroluminescent illumination and backlight which are highly demanded.

EXAMPLES

The features of the invention will be described more specifically with reference to Synthesis Examples and Examples below. The materials, processes, procedures and the like shown below may be appropriately modified unless they deviate from the substance of the invention. Accordingly, the scope of the invention is not construed as being limited to the specific examples shown below. The light emission characteristics were evaluated by using a source meter (2400 Series, produced by Keithley Instruments Inc.), a semiconductor parameter analyzer (E5273A, produced by Agilent Technologies, Inc.), an optical power meter (1930C, produced by Newport Corporation), an optical spectrometer (USB2000, produced by Ocean Optics, Inc.), a spectroradiometer (SR-3, produced by Topcon Corporation), and a streak camera (Model C4334, produced by Hamamatsu Photonics K.K.).

(Synthesis Example 1) Synthesis of Compound 4

A commercial product, 3,5-dibromotoluene (2.50 g, 10 mmol) was dissolved in 80 ml of dimethylformamide, tripotassium phosphate (12.74 g, 60 mmol), PdCl₂(PPh₃)₂ (dichlorobis(triphenylphosphine) palladium(II): 0.35 g, 0.5 mmol) and triphenylenyl boronate (5.44 g, 20 mmol) were added, and stirred at room temperature for 24 hours, and then reacted at 60° C. for 24 hours. The reaction solution was left cooled, 100 ml of water was added, filtered, washed with 50 ml of acetone, and further washed with 80 ml of water and 80 ml of methanol to give the compound 4 with a yield of 4.90 g, 90%. The reaction product was purified by reduced-pressure sublimation. MS (70 eV, EI) m/z=544 (M⁺).

(Synthesis Example 2) Synthesis of Compound 9

A commercial product, 3,3′,5,5′-tetrabromobiphenyl (1.41 g, 3 mmol) was dissolved in 120 ml of dimethylformamide, tripotassium phosphate (7.64 g, 36 mmol), PdCl₂(PPh₃)₂ (0.11 g, 0.2 mmol) and triphenylenyl boronate (3.27 g, 12 mmol) were added, and stirred at room temperature for 24 hours, and then reacted at 80° C. for 24 hours. The reaction solution was left cooled, 240 ml of water was added, filtered, washed with 200 ml of acetone, and further washed with 100 ml of water and 200 ml of methanol to give the compound 9 with a yield, 2.45 g, 77%. The reaction product was purified by reduced-pressure sublimation.

MS (MALDI) m/z=1059 (M+1).

(Synthesis Example 3) Synthesis of Compound 10

A commercial product, Br-triphenylene (3.07 g, 10 mmol) was dissolved in 80 ml of dewatered tetrahydrofuran in a nitrogen stream atmosphere, and kept at an internal temperature of −85° C. in an ethanol bath with liquid nitrogen. A hexane solution of n-butyl lithium (7.5 ml, 12 mmol) was gradually added to the solution, while kept at an internal temperature of −80° C. or lower. After 1 hour, a solution prepared by dissolving methyl chloroformate (1.42 g, 15 mmol) in 20 ml of dewatered tetrahydrofuran was added while kept at an internal temperature of −80° C. or lower, then kept at −85° C. for 1 hour, and thereafter stirred overnight at room temperature. 100 ml of water was gradually added to the reaction solution, filtered, and then washed with methanol and water to give the compound 10 with a yield of 1.21 g, 42%. The reaction product was purified by reduced-pressure sublimation.

MS (70 eV, EI) m/z=482 (M+).

(Example 1) Production and Evaluation of Organic Electroluminescence Device Using Compound 1

On a glass substrate with an anode of indium-tin oxide (ITO) formed thereon to have a thickness of 100 nm, each thin film was laminated according to a vacuum evaporation method at a vacuum degree of 5.0×10⁻⁴ Pa. First, HAT-CN was formed on ITO in a thickness of 10 nm, and then Tris-PCZ was formed thereon in a thickness of 30 nm. Next, a layer having a thickness of 30 nm was formed through co-evaporation with HK13 and the compound 1 from different evaporation sources, thereby forming a light-emitting layer. At this time, the concentration of HK13 was 6.0% by weight. Next, T2T was formed in a thickness of 10 nm, Bpy-TP2 was formed in a thickness of 40 nm, and further lithium fluoride (LiF) was deposited through vacuum evaporation in a thickness of 0.8 nm, and thereafter aluminum (Al) was deposited in a thickness of 100 nm, thereby forming a cathode to provide an organic electroluminescence device. The lifetime characteristic of the produced organic electroluminescence device, as measured at an initial brightness of 1000 Cd/m² and at a current density of 54.5 mA/cm², is shown in FIG. 2.

(Comparative Example 1) Production and Evaluation of Organic Electroluminescence Device Using Comparative Compound A (CBP)

An organic electroluminescence device was produced in the same manner as in Example 1 except that CBP was used to form a light-emitting layer in place of the compound 1. The lifetime characteristic of the produced organic electroluminescence device, as measured at an initial brightness of 1000 Cd/m² and at a current density of 54.5 mA/cm², is shown in FIG. 2.

The LT50 lifetime of the organic electroluminescence device using the comparative compound A was 12 days, but the LT50 lifetime of the organic electroluminescence device using the compound 1 was 277 days, that is, the latter device had a far longer lifetime.

(Example 2) Production and Evaluation of Organic Electroluminescence Device Using Composite Host Material of Compound 10 and CBP

An organic electroluminescence device was produced in the same manner as in Example 1 except that a light-emitting layer having a thickness of 30 nm was formed through co-deposition with HK13, the compound 10 and CBP from different evaporation sources, and the concentration of HK13 in the light-emitting layer was 1% by weight.

The voltage-current density characteristic of the produced organic electroluminescent device is shown in FIG. 3, the current density-external quantum efficiency characteristic thereof is in FIG. 4, the lifetime characteristic thereof is in FIG. 5, and the characteristic values thereof measured at 1000 Cd/m² are shown in Table 22.

(Comparative Example 2) Production and Evaluation of Organic Electroluminescence Device Using Comparative Compound A (CBP)

An organic electroluminescence device was produced in the same manner as in Example 1 except that CBP was used in place of the compound 1 to form a light-emitting layer and the concentration of HK13 in the light-emitting layer was 1% by weight.

The voltage-current density characteristic of the produced organic electroluminescent device is shown in FIG. 3, the current density-external quantum efficiency characteristic thereof is in FIG. 4, the lifetime characteristic thereof is in FIG. 5, and the characteristic values thereof measured at 1000 Cd/m² are shown in Table 22.

(Comparative Example 3) Production and Evaluation of Organic Electroluminescence Device Using Composite Host Material of Comparative Compound B and CBP

An organic electroluminescence device was produced in the same manner as in Example 1 except that a light-emitting layer having a thickness of 30 nm was formed through co-deposition with HK13, the comparative compound B and CBP from different evaporation sources, and the concentration of HK13 in the light-emitting layer was 1% by weight.

The voltage-current density characteristic of the produced organic electroluminescent device is shown in FIG. 3, the current density-external quantum efficiency characteristic thereof is in FIG. 4, and the characteristic values thereof measured at 1000 Cd/m² are shown in Table 22. The lifetime characteristic of the device was measured in the same manner as in Example 2, and LT50 thereof was 585 hours.

(Example 3) Production and Evaluation of Organic Electroluminescence Device Using Different Light-Emitting Material and Composite Host Material of Compound 10 and CBP

An organic electroluminescence device was produced in the same manner as in Example 2 except that YH016 was used in place of HK13.

The characteristic values of the produced organic electroluminescence device, as measured at 1000 Cd/m², are shown in Table 22.

TABLE 22 External Maximum Quantum Current Drive Current Power Emission LT50 Light-Emitting Efficiency Density Voltage Efficiency Efficiency Wavelength Lifetime Host Material Material (%) (mA/cm²) (V) (Cd/A) (lm/W) CIE (x, y) (nm) (H) ΔV Example 2 50% CBP:50% 1% HK13 3.4 15.2 5.6 6.7 3.8 0.55, 0.44 598 1050 — compound 10 Comparative CBP 1% HK13 1.6 29.6 8.5 3.3 1.3 0.53, 0.44 593 48 1.4 Example 2 Comparative 50% CBP:50% 1% HK13 2.2 24.1 7.2 4.1 1.8 0.55, 0.44 599 585 0.84 Example 3 comparative compound B Example 3 50% CBP:50% 1% YH016 4.5 14.3 5.3 7.0 4.2 0.58, 0.42 616 1550 — compound 10

The organic electroluminescence device using a composite host material of the compound 10 and CBP has a remarkably longer LT50 lifetime, as compared with the organic electroluminescence device using the comparative compound A (CBP) and the organic electroluminescence device using a composite host material of the comparative compound B and CBP, and can operate at a low drive voltage, and the current efficiency, the power efficiency and the external quantum yield thereof are all high values.

INDUSTRIAL APPLICABILITY

The compound of the invention is useful as a host material for delayed fluorescent materials. Accordingly, the compound of the invention may be effectively used as a host material for delayed fluorescent materials for organic light-emitting devices such as organic electroluminescence devices, etc. By using the host material for delayed fluorescent materials of the present invention, it is possible to provide an organic light-emitting device having a high efficiency, capable of operating at a low drive voltage and having a long lifetime. Thus, the invention has high industrial applicability.

REFERENCE SIGNS LIST

-   1 Substrate -   2 Anode -   3 Hole Injection Layer -   4 Hole Transport Layer -   5 Light-Emitting Layer -   6 Electron Transport Layer -   7 Cathode 

The invention claimed is:
 1. An organic light-emitting device comprising a layer that contains a delayed fluorescent material and a host material represented by the following general formula (1): (Tr)_(n)-Z  General Formula (1) wherein: Tr represents a substituted or unsubstituted triphenylenyl group, and plural Tr's existing in the general formula (1) may be the same as or different from each other; Z represents a carbonyl group or a substituted or unsubstituted, n-valent aromatic hydrocarbon group; n represents an integer of 2 to 6, but when Z is a carbonyl group, then n is 2; and the substituted n-valent aromatic hydrocarbon group is a n-valent aromatic hydrocarbon group substituted by a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, an alkyl-substituted amino group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an alkylsulfonyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an amide group, an alkylamide group having 2 to 10 carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, a trialkylsilylalkyl group having 4 to 20 carbon atoms, a trialkylsilylalkenyl group having 5 to 20 carbon atoms, a trialkylsilylalkynyl group having 5 to 20 carbon atoms, a nitro group, or a substituent represented by the following general formula (2): Tr⁴-CO—  General Formula (2) wherein Tr⁴ represents a substituted or unsubstituted triphenylenyl group, provided that when Z is a substituted or unsubstituted, n-valent aromatic hydrocarbon group, then at least one of the following conditions is satisfied: <1> at least one Tr is a substituted triphenylenyl group, and <2> Z is the substituted aromatic hydrocarbon group, and provided that at least one of the following conditions is satisfied <A> Z is an n-valent aromatic hydrocarbon group substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group, <B> Z is a carbonyl group, <C> at least one Tr has a substituent represented by the following general formula (2): Tr⁴-CO—  General Formula (2) wherein Tr⁴ represents a substituted or unsubstituted triphenylenyl group, and <D> at least one Tr is a triphenylenyl group substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
 2. The organic light-emitting device according to claim 1, wherein Z is a substituted or unsubstituted, n-valent aromatic hydrocarbon group.
 3. The organic light-emitting device according to claim 2, wherein Z is an n-valent benzene residue.
 4. The organic light-emitting device according to claim 3, wherein Tr bonds to the 1-position and the 3-position of the benzene residue.
 5. The organic light-emitting device according to claim 2, wherein Z is an n-valent biphenyl residue.
 6. The organic light-emitting device according to claim 2, wherein Z is an n-valent aromatic hydrocarbon group substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
 7. The organic light-emitting device according to claim 1, wherein Z is a carbonyl group.
 8. The organic light-emitting device according to claim 7, wherein at least one Tr has a substituent represented by the following general formula (2): Tr⁴-CO—  General Formula (2) wherein Tr⁴ represents a substituted or unsubstituted triphenylenyl group.
 9. The organic light-emitting device according to claim 8, wherein two Tr's have, in total, 1 to 5 substituents each represented by the general formula (2).
 10. The organic light-emitting device according to claim 7, which contains a partial structure with a carbonyl group bonding to the 2-position, the 3-position, the 6-position, the 7-position, the 10-position or the 11-position of the triphenylene ring inside the molecule.
 11. The organic light-emitting device according to claim 10, wherein all the carbonyl groups bonding to the triphenylene ring existing inside the molecule bond to the 2-position, the 3-position, the 6-position, the 7-position, the 10-position or the 11-position of the triphenylene ring.
 12. The organic light-emitting device according to claim 1, wherein at least one Tr in the general formula (1) is a triphenylenyl group substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
 13. The organic light-emitting device according to claim 1, which is an organic electroluminescence device.
 14. A compound represented by the following general formula (3): Tr¹-CO-Tr²  General Formula (3) wherein Tr¹ and Tr² each independently represent a substituted or unsubstituted triphenylenyl group, and Tr¹ and Tr² may be the same as or different from each other.
 15. A compound represented by the following general formula (4): (Tr³)_(n1)-Z¹  General Formula (4) wherein Tr³ represents a substituted or unsubstituted triphenylenyl group, and plural Tr³'s existing in the general formula (4) may be the same as or different from each other; Z¹ represents a substituted or unsubstituted n-valent aromatic hydrocarbon group; n1 represents an integer of 2 to 6; at least one of Tr³ and Z¹ is substituted with a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group; when Tr³ is unsubstituted, then Z¹ is a benzene ring residue substituted with a phenyl group or a methyl group and bonds to Tr³ at the 1-position and the 3-position, or is a biphenyl residue substituted with a phenyl group, provided that when Tr³ is a substituted triphenylenyl group, the triphenylenyl is substituted at at least one of 6-, 7-, 10- and 11-positions by a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, an alkyl-substituted amino group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an alkylsulfonyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an amide group, an alkylamide group having 2 to 10 carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, a trialkylsilylalkyl group having 4 to 20 carbon atoms, a trialkylsilylalkenyl group having 5 to 20 carbon atoms, trialkylsilylalkynyl group having 5 to 20 carbon atoms, a nitro group, or a substituent represented by the following general formula (2): Tr⁴-CO—  General Formula (2) wherein Tr⁴ represents a substituted or unsubstituted triphenylenyl group. 